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Rockport Family & Kid Friendly Rentals

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    Travelers to Rockport are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in RockportView all 63 rentals
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    The Sail Loft of Bearskin Neck1 / 17
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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...
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    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...
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    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Back Beach Cottages - Charming house & guest house1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2017
    There are two cottages located on the same property. The ocean views are amazing and downtown Rockport is just a short walk away.
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    About this property
    Back Beach Cottages are a unique 2 cottage property with stunning views of the ocean. The location offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The homes are steps away from Back Beach, a 5 minute walk to Front Beach and...
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    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Private Yard
    • Air Conditioning
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    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...
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    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...
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    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2018
    What a wonderful place!! I had the upstairs to myself as well as a living room. Wendy has thought of everything! Very hospitable. I wish I could have stayed here for a month...
    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...
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    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...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • 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...
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    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...
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    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    Our third Year at The Seaward, Nancy is a fantastic host, always. We love the apartment, and it always feels like we are at home. The weather was beautiful as always and the...
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    About this property
    This newly renovated ocean view apartment at the Seaward exudes classic coastal charm. Here you will fully relax while listening to the ocean waves. Lover’s Cove features exposed brick walls, newly conditioned hardwood floors and a king bed. This seaside apartment makes for our most spacious...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
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    • 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...
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    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Grill
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    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...
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    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...
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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
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    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious seaside apartment offers 2 bedrooms, 2 bathrooms, and living room/kitchen with a sunny ocean view dining/game area within a bay window. At over 800 square feet it is our largest accommodation. You’ll enjoy Gap Cove’s seaside charm, with amenities including free WIFI, DVD player,...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    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...
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    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...
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    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My ocean view house with beautiful vistas was built by the Rockport Granite Company in 1817. It is a comfortable and bright 3 story house that can sleep 8, it has 4 bedrooms, 2 bathrooms, and 3 decks. The house in the scenic New England coastal town of Rockport, MA. P.S. The interior of the house...
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    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Year-Round Vacation Home1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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...
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    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...
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    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2017
    Parking was a little tricky and I have to say I was quite concerned when we first arrived. However, Tim was there to greet us and made sure we found appropriate parking for all...
    Reviewed August 7, 2017
    The Beach & King is the perfect vacation home for our four generation family. The house is spacious and beautifully decorated. The front porch is a lovely spot to enjoy...
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    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village....
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    Rockport, Cape Ann 01966
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Private Yard
    • Grill
    • Waterfront
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Last week of Aug. and all of Sept still AVAILABLE. Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full bathrooms, non obstructed Ocean View House on a rise overlooking...
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    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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....
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    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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. Three fabulous decks each w/an incredible ocean or Pigeon cove view. Each residence has three bedrooms (two large bedrooms and bedroom/office). Office...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Directly on Long Beach Rockport MA1 / 46
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Internet Access
    • Central Heating
    • Patio
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 20, 2017
    The location of the house is absolutely magnificent. 3rd house from the end of the Longbeach road, you have an amazing view of the sea. The house on 3 floor is enough big to...
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    About this property
    Waterfront Home on Beautiful Long Beach on Cape Ann Fully renovated for 2016, this light-filled, three-level beachfront home sits on the seawall above sandy Long Beach. We're at the Rockport end with no second-row cottages behind. Views of the ocean, beach and marsh greet you through large...
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    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Patio
    • Grill
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    • 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...
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    Rockport, Cape Ann 01966
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Season-June through September- one week left in September --9/15 to 9/22 Directly on the Atlantic with spectacular ocean views opposite Thatcher’s Island’s Twin Lights. Relax on the wooden deck off the 16 foot sliding glass doors from the living room/dining room. On the right of the house is...
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    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
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    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...
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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright colors, rich fabrics, and antique furnishings make this three-bedroom home truly special. Enjoy a variety of amenities, including a full kitchen, a lush yard, and a patio with a gas grill, all three short blocks from the beach. Located on a quiet residential street, this Rockport home is...
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    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Parking
    • Washer
    • Internet Access
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Trade the stress of daily life for a laid-back retreat on the New England coast when you stay at this charming Rockport vacation rental. Up to 12 guests will enjoy home comforts such as a private washer/dryer and free WiFi, not to mention a beautifully styled interior and a spacious deck with ocean...
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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to the very best of Rockport from this charming family home, an airy, quaint New England escape with private parking, a private patio and gas grill for summer barbecues, a dog-friendly living space, and a prime location within blocks of the beach, the harbor, and local shops and restaurants....
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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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