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Cape Ann Elder Access Vacation Rentals

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    Travellers to Cape Ann are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    42 Matching Rentals in Cape AnnView all 157 rentals
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    The Pratt House on the Boulevard1 / 25
    (10)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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....
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Salty Dog Summer Stay at Old Garden Beach1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    Reviewed 27 June 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed 19 February 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
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    About this property
    Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing spectacular views of...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Back Beach1 / 15
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    Reviewed 24 August 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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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Ocean Views
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Season-June through September- Aug 26 to Sept 9 (2 weeks in a row); 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 a...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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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    Reviewed 27 October 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Completely renovated 2 bedroom, 1.25 bath. 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 drive to Train...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can't get any closer to New England charm than this condo, called Four Winds, located on Tuna Wharf off Bearskin Neck in Rockport, MA. The view looks directly over the water and is truly picturesque. This is a great place for a getaway providing the choice of cooking in or enjoying the many...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Ocean Views
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    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
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    About this property
    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 the Atlantic and Rockport's famous Thatcher Island twin...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    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”...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
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    About this property
    $1,600 (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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *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 the beach, full...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Grill
    • Secure Parking
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    • Waterfront
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    Pet friendly
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    About this property
    A large, bright and cheery front bedroom with two Queen size beds – private bath with clawfoot tub and shower. Newly constructed bathroom with vintage fixtures and repurposed woods. Our breakfast room has old pine cupboards, creeping ivy with twinkling lights, lace tablecloths and original vintage...
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    Essex, Cape Ann 01929
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Quiet Intown Cottage by Front Beach1 / 7
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
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    • Shared Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2016
    The owner of this property covered it all - stocked the kitchen with fruit and cheese, eggs, milk,cheerios,English muffins and ice in the freezer to get you started until you...
    Reviewed 17 August 2015
    I booked this property based on a few reviews form other vacationers. The location and cottage itself truly exceeded our expectations. The owner, Judy, was wonderful and so very...
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    About this property
    Inquire Winter Rates Specials Just as sweet as icing on a cupcake - This downtowner located in a court yard makes a perfect getaway since you can stroll to the beach and to all the cultural and seafood eateries located within a stones throw of your front door. The CORNERed INn is designed...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Charming 3 bdrm cottage located in downtown Rockport. Come enjoy this quiet, private oasis set back from the street and surrounded by gardens and trees but still within walking distance to downtown, beaches and the train to Boston. This house is a unique blend of new and old. Built 7 years ago with...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
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    • Satellite TV
    • Balcony
    • Central Heating
    • Ocean Views
    • Patio
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    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Completely renovated 3-4 bedroom, 1.5 bath. Spacious designer kitchen w/ stainless steel appliances. Large Living room, Dining Room, Family Room (optional bedroom) (first floor) and three bedrooms (second floor). Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    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...
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    Essex, Cape Ann 01929
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Back Beach Cottages - Charming house & guest house1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
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    Pet friendly
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    Reviewed 30 January 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    One bedroom loft apartment located in the lower barn. Queen size bed, sleep sofa, full kitchen and bath. Back deck open to pristine pastures and hiking trails. Cathedral ceilings with skylights and 8 foot sliding doors bring the outside in. Watch for deer, wild turkey and plenty of birds in the...
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    Essex, Cape Ann 01929
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    • Ocean Views
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    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Smoking allowed
    About this property
    Our Bed & Breakfast is located in the small New England coastal town of Essex, MA. on Cape Ann. Historic farmhouse built in 1695 on 18 pristine areas of forest, fields and meadows. First free school in state. Front field used during Revolutionary War for militia training. House completely updated...
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    Essex, Cape Ann 01929
    Private Room - 3 Bedrooms, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    My place is close to the full Atlantic, beaches, restaurants. You’ll love the comfy bed, quiet house, and spacious accommodations. The immediate neighborhood offers great walks by the ocean, miles of woodland trails through Ravenswood Park and other nearby open spaces. Magnolia Beach offers public...
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    Gloucester, Cape Ann 01930
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Mermaid suite, at Changing Tides Bed and Breakfast, features a comfortable king sized sleep number bed. The large sunny room features a sky light, a ceiling fan, AC, and a large ensuite bathroom. Stay includes daily multi-course gourmet breakfast. Beaches, downtown shops and galleries, and the...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Central Heating
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Ocean Views
    • Grill
    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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....
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your life. The home is situated between two of Cape Ann's most coveted beaches, Long Beach and Good Harbor Beach. The home is a stones throw away from an ice cream stand and pizza shop....
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 8 Bedrooms, 2 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect place to relax in Rockport this fall. This cottage offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The cottage is steps away from Back Beach, a 5 minute walk to Front Beach, and a 10 minute walk to the heart of...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Grill
    • Patio
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage was built in the 1920s and recently renovated. At the end of a long driveway on the back of an old estate, it is very private and yet within 10 minutes walk of Singing Beach and less than a mile from the town of Manchester. So there is easy access to shops, restaurants, and even...
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    Location Information
    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Patio
    • Grill
    • Balcony
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gloucester, America’s oldest seaport! This two acre, family-friendly, contemporary private retreat on Gloucester’s Rust Island offers 4 Bedrooms with stunning panoramic views of beautiful marshes and the Jones River, which flows into the Annisquam River and Ipswich Bay. Surrounded by...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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