We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cape Ann Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $378 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Cape Ann are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 151 Rentals in Cape Ann
    Sort by:
    Default
    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Periwinkle Cottage - Unit 11 / 23
    (32)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Waterfront 2 Bedroom !1 / 14
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 22, 2018
    We stayed here for a family wedding in Sept. 2017. The apartment was a perfect location(wedding was 8-mns away). It was very well maintain and very,very clean. (Which is our No...
    Reviewed May 2, 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
    See all reviews
    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2017
    We had a fantastic holiday in Gloucester. Summer wind was the perfect location - the house was beautiful, with all mod cons and fabulous views over the harbour. It was also...
    Reviewed May 24, 2017
    We recently stayed at Summerwind Cottage in Gloucester MA. We thoroughly enjoyed our stay. The decor was wonderfully New England cottage. The living area was cozy with lots...
    See all reviews
    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Balcony
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Mark's rental apartment in Gloucester is my all-time favorite rental home! It offers a comfortable queen-sized bed, an additional bedroom with a twin, a living room with a small...
    Reviewed October 5, 2017
    When we arrived our host met us at the door and let us in, the first thing we noticed was the wonderful view and a balcony to sit on. We were close to most places by walking.
    See all reviews
    About this property
    Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 chairs. Great views of White...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
    See all reviews
    About this property
    Formerly Seaward Inn, 'The Seaward' continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
    See all reviews
    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed October 5, 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
    See all reviews
    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Inquiry
    Save time - get the best Cape Ann rentals sent straight to your email!
    Get the List
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 2+ bedroom, 1.25 bath. Second floor unit. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minute walk (1.2 mile) 2 minute...
    View all property information
    Location Information
    Manchester-by-the-Sea, Cape Ann 01944
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 19
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed November 24, 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
    See all reviews
    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
    See all reviews
    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
    Reviewed September 20, 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
    See all reviews
    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
    Reviewed July 2, 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
    See all reviews
    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Dragonfly1 / 7
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Yard
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 6, 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed August 30, 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
    See all reviews
    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated home. New to the 2014 season. Great for families. Rent just one town-home or rent the entire town-home w/ friends or family. This listing is for the first floor. Each residence has three bedrooms (two large bedrooms and bedroom/office). Office can be used as a third bedroom....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Beachcomber Suite1 / 11
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 3, 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed July 19, 2016
    It was wonderful to be with Stephanie and Jay - their home is beautiful and welcoming. Stephanie's breakfast is not to be missed! I especially enjoyed the outdoor spaces - the...
    See all reviews
    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes daily multi-course gourmet...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Yard
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 1, 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed October 25, 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
    See all reviews
    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Lovely 'Blue Heron Cottage' on Annisquam River!1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 19, 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
    See all reviews
    About this property
    Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed January 27, 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
    See all reviews
    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    A Year-Round Vacation Home1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 2017
    5 adultsHouse is in a great location.Very uncomfortable beds unfortunately. (In all rooms!) -wished there was a queen bed instead of a double in ocean view room-) there...
    See all reviews
    About this property
    $1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining room, and a masonry fireplace in...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2016
    This simple seaside cottage is well situated to some lovely views of the coast, including the light houses of Thatcher Island. The cottage itself is well-maintained with a very...
    See all reviews
    About this property
    Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of the Thacher’s Island Twin...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed July 7, 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
    See all reviews
    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 27, 2016
    We just completed our first visit here and plan to return to this house. A Very clean, historic home that more than met our expectations. It is off the beaten path with both...
    See all reviews
    About this property
    Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second floor bathroom is a large...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    One Bedroom Loft Apartment B at Cedar Hill Farm B & B1 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2017
    This was our first stay in a B&B, it did not disappoint! It was very clean, cozy and conveniently located to the town of Essex. Appreciated the breakfast choices, especially...
    See all reviews
    About this property
    We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and meadows. Guests can enjoy...
    View all property information
    Location Information
    Essex, Cape Ann 01929
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport in town private cottage within walking distance to town and all Rockport has to offer: beaches, restaurants, art galleries, shops, Shalin Liu performing arts center, Bearskin neck and the train. *The cottage is 2 floors. On the first floor is a fully equipped kitchen, with a cooler for...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Wi-Fi
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann, MA Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Golden Sands is the quintessential turn of the century Gloucester beach 'cottage.' With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house. The main level includes...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1750, this charming vacation rental provides lovely views of the Essex Salt Marsh and is centrally located to everything Essex has to offer. Indigo Blue is steps away from downtown Essex, with its numerous restaurants and a wide assortment of antique shops. Indigo Blue is also perfectly...
    View all property information
    Location Information
    Essex, Cape Ann 01929
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Inquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch spectacular sunsets over the Essex River from the expansive deck of this one-of-a-kind vacation home. Clamshell Landing sits on 22 acres of pristine conservation land and overlooks the green grasses of the Essex salt marsh. Swim or kayak to the beach or out to lunch in Essex by way of the...
    View all property information
    Location Information
    Essex, Cape Ann 01929
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North Shore, with 1.5 miles of pure...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 4 bedroom, 2 bath. Extraordinary home build in 1917. Incredible workmanship. Spacious designer kitchen w/ stainless steel appliances. Large Living room, Dining Room, and fours bedrooms (second floor). Central A/C! Close to town center, commuter rail, and Singing Beach. 4...
    View all property information
    Location Information
    Manchester-by-the-Sea, Cape Ann 01944
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Private Yard
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 14, 2017
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed March 15, 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
    See all reviews
    About this property
    Are you looking for a conveniently located affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout, and with 4...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Inquiry
    Sea Mist Cottage1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 11, 2017
    We came to celebrate our 32nd anniversary. We absolutely loved the Seamist cottage. There were did many wonderful details that were put into this place, we couldn't list them...
    Reviewed August 14, 2017
    We were extremely happy with our stay. The cottage was very clean and had an ocean theme through out. Everything we needed was there! Our daughter (14) slept in the loft and...
    See all reviews
    About this property
    Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, welcome inquiries & feedback....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Granite Pier is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is quintessential New England with...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downstairs (which was built in...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your days at the beach or relaxing poolside by your very own private pool. Rockport Hideaway is also only a short distance from Rockport's shopping, dining and family activities. Leave the car and stroll to the village, beaches, schools (with tennis courts and playground), and the commuter...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meet Me on South Street is a charming condo in a 2 unit antique colonial building that is one of Rockport's finest examples of Early American architecture. Lovingly and painstakingly renovated, this two-bedroom getaway is tastefully furnished and comfortable. A sunny pied-à-terre, it is just the...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    1
    Cape Ann Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    69° 50°
    June
    75° 55°
    July
    74° 55°
    August

    Additional Cape Ann Info

    Go to map view
    • Local time: 09:29 PM (EDT)
    List your property
    Owner log in