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.

Gloucester Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
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
    Price
    per night
    $410 Average
    $0$1,000+
    Suitability
    More filters
    All 126 Rentals in Gloucester
    Sort by:
    Default
    Travelers to Gloucester are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    10 Reviews
    5 Bedrooms, Sleeps 12Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    16 Reviews
    2 Bedrooms, Sleeps 4Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    8 Reviews
    2 Bedrooms, Sleeps 7Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    4 Reviews
    4 Bedrooms, Sleeps 8Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed November 17, 2014
    Beautiful home. Open beam construction. Impressive wooden entry door with iron work fixtures. Soothing relaxing music playing in the breakfast room. Walled in yard with gated...
    Very good of 5 bubbles
    Reviewed September 6, 2014
    We found the house to be in good order. The kitchen had everything we needed to cook once in a while when we didn't dine out. The bathrooms and bedrooms were nice and clean...
    See all reviews
    About this property
    LAST MINUTE CANCELLATION allows summer RATE DISCOUNT on authentic English Manor Home reminiscent of the Cotswolds. 'Misselthwaite Manor' is a a quiet respite in a busy world, yet close to everything Historic Gloucester has to offer. Located in the heart of the private peninsula of Eastern...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    3 Reviews
    1 Bedroom, Sleeps 3Quick 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
    Very good of 5 bubbles
    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...
    Excellent of 5 bubbles
    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, Sleeps 4Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • 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
    5 Reviews
    1 Bedroom, Sleeps 2Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed September 9, 2015
    This place is so well-located, well-designed, comfortable and easy! It allowed us a much needed break with access to all the beauty of Gloucester. I loved rocky neck, biking to...
    Excellent of 5 bubbles
    Reviewed August 5, 2015
    This is the perfect cottage for a couple retreat. It is a home away from home. Conveniently located for walks and picture taking. We will defintely stay here again when we...
    See all reviews
    About this property
    Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on East Main street, busy during the day, quiet at night. Close to everything by foot or bicycle. Sunny, furnished, adorable 1BD. Living Room/Kitchenette downstairs, Bedroom/Bath...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick 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
    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
    5 Bedrooms, Sleeps 13Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 13
    Make Inquiry
    4 Reviews
    2 Bedrooms, Sleeps 4Quick 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
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 weeks ago
    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...
    Excellent of 5 bubbles
    Reviewed June 25, 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    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
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    2 Reviews
    6 Bedrooms, Sleeps 12Quick 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
    • Satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Very good of 5 bubbles
    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
    15 Reviews
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed July 2, 2013
    My family and I have stayed at Good Harbor house for the past five or six years. We have been coming to Gloucester every year for more than 20 years. Good Harbor house is...
    See all reviews
    About this property
    This tastefully decorated, immaculate one-bedroom vacation rental is on the first floor of a landmark Victorian, with private entrance off a grand wrap-around covered veranda, overlooking private fenced-in lawn and garden. The covered veranda provides a great cooling respite from the sun in summer...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Reviews
    5 Bedrooms, Sleeps 11Quick 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
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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
    Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, dryer. Three fireplaces,...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Inquiry
    Studio, Sleeps 2Quick 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. Walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor House”...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate 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...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A tastefully renovated vacation home, Victorian House on Rocky Neck (Gloucester’s fabled artist colony) has three bedrooms and a gorgeous front porch overlooking the water. From the porch, step into the home’s front hall and formal living room, complete with a custom delicately-tiled fireplace....
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet and comfortable waterfront vacation rental cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. The main floor of the home consists of a charming open living and dining area, a small but well-equipped kitchen, a half bath, a screened...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Balcony
    • Internet Access
    • Satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and recently renovated vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    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, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Patio
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficiently and effectively packs a...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. This gracious home gives hints to a bygone era while offering modern amenities. A...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Inquiry
    1 Bedroom, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Porch
    • Air Conditioning
    • Washer
    • Satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting directly on the the beautiful port of Gloucester Harbor, this light and airy 3 room apartment offers full private bath, fully applianced kitchen, king bed and wonderful sitting porch. Walk or bike to local restaurants, museums, theatre and beach, and enjoy all that is Gloucester. The...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of storage, a gas range, and a small...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sandbars. Walk from this...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    6 Bedrooms, Sleeps 16Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and gracious vacation rental home offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family or your extended group of up to 16, making it the perfect getaway for family reunions or vacations with friends. The house has been...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Front row seats from every room and deck to view glorious evening sunsets over the Annisquam River and Ipswich Bay. Sunset Cottage is a charming 2 bedroom, 1 bath cottage on Gloucester’s Thurston Point that sits directly on the tidal Annisquam River and boasts unparalleled views. Two decks with...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    5 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    5 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines is situated on over an acre of waterfront land and has lovely gathering spaces both inside and out. It was built as an impressive yet casual vacation home to entertain the family...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the coast, the...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway....
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • 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, 4 Bathrooms, Sleeps 12
    Make Inquiry
    5 Reviews
    4 Bedrooms, Sleeps 7Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Ocean Views
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed February 3, 2015
    We try to stay here every year because we love the comfortable quality of a vacation home that's been in the family since 1929. The roomy screened in porch wraps around 3...
    See all reviews
    About this property
    Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 to December 31. This newly renovated and updated waterfront gem has four bedrooms and 1.5 baths, a deep-water dock (accommodates up to a 30 foot boat, with our new extended dockage in 2014) and a...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    2 Reviews
    6 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    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...
    Excellent of 5 bubbles
    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, Sleeps 12
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    1 Bedroom, Sleeps 3Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 4, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    1 Review
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    Reviewed July 29, 2015
    Cute house with a terrible parking/road situation. Poorly maintained exterior and patio made walking around the TINY yard dangerous for kids and those with mobility/vision...
    See all reviews
    About this property
    A pleasantly bright vacation home situated in Gloucester's charming Bay View neighborhood, Annie's Place radiates an aura of sun and warmth. Only a 10-minute walk to lovely Plum Cove Beach, Annie's Place lets you spend your summer vacation relaxing, discovering local fauna such as hermit crabs, and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    4 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2016! Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! If you would like to stay mere steps from Long Beach, this elegantly appointed townhouse is the place for you! Close to white sands and lively surf, you will enjoy the scenic seascape year round watching surfers ride the waves from your top-floor deck. At the heart of this multi level...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Balcony
    • Satellite TV
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! This bright and open contemporary vacation rental home is the perfect home base for multiple families or groups, having two living rooms and two dining rooms and plenty of space to stretch out. There is also access to private Coffins Beach; choose to walk the .7 miles to the beach, or...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New for 2017! Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable vacation rental home. Spend the day at the beach where you can swim, soak in the sun, or walk at low tide out to picturesque Salt Island. Prefer to stay at the house?...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    1 Bedroom, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Washer
    • Satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or tie up your boat to its 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...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Previous
    Gloucester Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    59° 40°
    May
    69° 50°
    June
    75° 55°
    July

    Additional Gloucester Info

    View Map
    • Local time: 08:43 AM (EDT)
    List your property
    Owner log in