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Manchester-by-the-Sea House Rentals

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    Don't let other travellers get your favourite Manchester-by-the-Sea area vacation rental. You're so close to securing your perfect getaway. Book today.
    97 Matching Rentals in the Manchester-by-the-Sea AreaView all 165 rentals
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    Manchester-by-the-Sea
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Manchester-by-the-Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Manchester-by-the-Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 15 kilometres of Manchester-by-the-Sea.
    Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Welcome to Broom & Board. As you enter through the antique front door, you are greeted by a vestibule that cherishes history while celebrating modern conveniences. Special Note: pictures depict pre renovation home. Home has been recently renovated and re-furnished. New pictures should be posted...
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    Salem, Massachusetts 01970
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed August 3, 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Salem
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Belle Femme is located in the McIntire Historic District of Salem, next to many historic, cultural and wedding venues. What a great space to share an extended family vacation or celebration – there’s room for everyone: grandparents, siblings, cousins. Belle Femme provides 18th century open concept...
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    Salem, Massachusetts 01970
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
    Hillside Ocean View 2BR with Private Beach Access1 / 40
    (1)Excellent
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Balcony
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2018
    Thank you Mark for your hospitality, the cottage was a wonderful experience to show grandchildren what growing up in Ipswich is all about. The thoughtful amenenities...
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    About this property
    Set upon Great Neck hill, this antique winterized cottage has a great ambiance and a nice view of the water where the Atlantic meets the mouth of Ipswich River. Spacious and fun for families and small groups, you can walk right down to Pavilion Beach within 10 minutes and access to famed private...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Waterfront Woodsy 3BR Cottage1 / 68
    (1)Excellent
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
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    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Special -See Gardens of Marblehead Bloom, 4 min Walk to Beach, Private Patio-Bra1 / 46
    (1)Excellent
    Marblehead
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed January 4, 2019
    We enjoyed every moment of our stay at Brackett Cottage and couldn’t have asked for more. Exquisitely decorated with antiques and period pieces, this is a fully functional...
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    About this property
    Nestled in the heart of historic old town Marblehead, Brackett Cottage is a mere 1-minute walk to shops and restaurants. A 5-minute walk takes you to a beach on Marblehead's famous harbor. While away a perfect day, watching sailboats and schooners soar past. A visit to Brackett Cottage of...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The dining area and deck overlook a gardeners delight of perpetually blooming flowers surrounding a Koi pond a beautiful woodsy backdrop - the backyard is a slice of heaven, and yours to enjoy when you stay at Serenity. This home is nestled in a quiet neighborhood surrounded by attractions like...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beverly
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    Try to imagine your own fisherman's cottage transformed into a quaint modern waterfront home ... that's Riverside Retreat. A beautifully appointed home with 4 levels of outdoor waterfront living: rock on the back porch; dine on the stone patio; lounge on the large deck; take the gangplank down to...
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    Beverly, Massachusetts 01915
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beverly
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Try to imagine a location with all the urban conveniences in a cozy neighborhood - that's RiverView! Nestled in a protected peninsula of Beverly, RiverView provides the perfect get-away location. The home is just around the corner (a 1 minute walk) from a riverside playground & beach with great...
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    Beverly, Massachusetts 01915
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Salem
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    The 1813 Daniel Lawrence House This charming house built in 1813 has been updated for modern living in the heart of Salem. The first floor of this home features a living room with original hardwood floors overlooking historic Derby Street and a fully equipped kitchen. This home also boasts a...
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    Salem, Massachusetts 01970
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Marblehead
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Nestled in the heart of historic old town Marblehead, Rockmere Inn is a 1-minute walk to boutiques and restaurants, a 5-minute walk to Marblehead's famous harbor, and amidst a lovely stroll in the historic village. Wander along the streets of Marblehead and be transported back to colonial times....
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Atlantic Highlands Apartment Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Marblehead
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Try to imagine a cozy home on a quiet side street in the heart of Marblehead's historic center - that's Leeward! Marblehead Harbor, Boston Yacht Club, Abbot Hall, Jeremiah Lee Mansion, King Hooper Mansion, & Crocker (Seaside) Park are all within a 5 minute walk. This location cannot be beat!...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    A Glamorous Gloucester Getaway Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront Cape Ann retreat w/ stunning  views, fireplace, deck, & gas grill!1 / 30
    (1)Excellent
    Rockport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Ocean Views
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    We made this rental last minute and were so glad that we were able to get it. It has a wow factor when you arrive. The back deck faces east, so you get the benefit of seeing a...
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    About this property
    Breakwater House Go on a classic New England retreat and enjoy a luxurious stay at this lovely Cape Ann home. You'll have amazing oceanfront views, a cozy wood-burning fireplace, and a great deck with a gas grill for outdoor entertaining. This house is located in Rockport, MA, just 43 miles...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
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    Waterman's View Cottage Let the stress melt away in the tranquil Atlantic breeze when you book your well-deserved getaway to this family-friendly Gloucester cottage. With soothing ocean views, access to a pristine private beach, and a peaceful location in a quiet neighborhood, you may never want to...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Rockport
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanfront Cottage - Long Beach Come and get away from it all at this beautiful beachfront property in Rockport, where you'll be mere steps from the open, sandy expanse of Long Beach! Let the sights and sounds of the Atlantic Ocean wash away your stresses as you take long morning walks along the...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Vintage Rockport Escape Bright colors, rich fabrics, and antique furnishings make this three-bedroom, dog-friendly 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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Rockport
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    Annetti's Watch 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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Starfish Cottage 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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanview Oasis This gorgeous home by the water is the perfect getaway for you and your family! Boasting beautiful views from the back deck, you'll barely want to leave your home! This rental has a full kitchen with everything you might need to whip up a quick meal along with plenty of space for...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Relax and enjoy the summer in Marblehead1 / 16
    (2)Excellent
    Marblehead
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
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    Reviewed June 25, 2017
    What a lovely, homey place to stay for 4 adults and 2 children! A beautiful home, well furnished, tastefully decorated, clean and cozy, in a quiet neighborhood. Plenty of...
    Reviewed August 14, 2015
    Wow! Great summer stay and family reunion in Marblehead, thanks in no small part to this absolutely pristine home. The photos do NOT do this home justice. The feel is...
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    About this property
    Located only three blocks from Devereux beach and ln a quiet neighborhood, our house, renovated in 2014, is the perfect getaway for the summer. It is walking distance to downtown Marblehead, restaurants to a movie theater...The house, fully renovated in 2014 can comfortably accomodate 6 people. The...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    Gloucester
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 1, 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed October 25, 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
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    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located right around the corner from Gloucester’s fabled Stacy Boulevard, this completely renovated vacation rental home provides convenient access to downtown Gloucester. Gloucester Harbor and Stage Fort Park, with its beaches and playgrounds, are just a short stroll away and Main Street's shops,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Rockporter is a charming waterfront vacation rental home that sits on a quiet lane in Rockport's Pigeon Cove. You'll be as close to the ocean as one can be on Cape Ann, enjoying sweeping views of Sandy Bay from most rooms in the house. Set up to comfortably sleep 7, the house has an eat-in...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    Gloucester
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed July 7, 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Marblehead
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
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    About this property
    Located on Marblehead Neck, just a short walk to the harbour, you'll find all you need to enjoy a luxurious stay in this grand New England home. All the comforts you need are provided in a clean and functional home. Top quality outfitting for everything. I'll personally make sure you have all you...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Beautifully Renovated Antique Home1 / 21
    (1)Excellent
    Marblehead
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Central Heating
    • Housekeeping Included
    • Wi-Fi
    • Washer
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2015
    A week was not long enough! We had a wonderful time staying here. Spaciaous, clean, lovely inside and out. Salem is a hop, skip, and jump away, and we also took the train into...
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    About this property
    Vacation in beautiful Marblehead in this wonderfully updated furnished Victorian. Located on a quaint side street only a stones throw to downtown, this 4 bedroom, 2 bath beautiful single family home is sure to help create lasting vacation memories. Carefully renovated chefs kitchen, beautifully...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Marblehead
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor private guest bedroom with...
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    Location Information
    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Back Beach1 / 15
    (2)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Rockport
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and fully air conditioned vacation home boasts a lovely landscaped in-ground pool in a private, fenced-in yard. In the center of charming Rockport, the home is only two blocks from Old Garden Beach and Rockport harbor. A short stroll takes you to Bearskin Neck and its shops,...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beverly
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a cul de sac and fronting on the Crane River, Afternoon Delight in historic Beverly is the perfect place to watch the river currents glide by. The riverfront wraparound deck offers a blissful place to sit or dine in either sun or shade, thanks to an exterior awning. In the garden, the...
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    Beverly, Massachusetts 01915
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Washer
    • DVD Player
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Essex
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch spectacular sunsets over the Essex River from the expansive deck of this one-of-a-kind vacation home. Clamshell Landing sits on 22 acres of pristine conservation land and overlooks the green grasses of the Essex salt marsh. Swim or kayak to the beach or out to lunch in Essex by way of the...
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    Essex, Cape Ann 01929
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Rockport
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Rockport's 'the Avenues,' this home offers a quiet and peaceful environment. It is perfect for those who are trying to find a retreat from the everyday noise of the busy city. Stroll along the scenic streets or along the fabled coastal Atlantic Path, a glorious oceanfront walk over the...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanside at Good Harbor is a waterfront vacation home directly on Good Harbor Beach, Gloucester's finest stretch of sand. Gracious and beloved, this family-friendly five bedroom summer cottage is set on picturesque Brier Neck. Sit on the waterfront terrace/patio and enjoy the summer breezes and...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
    Cool Cove: Wingaersheek Beach plus your own private beach & all those views!1 / 21
    (1)Very good
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 30, 2019
    The house had a sugar ant problem, toilets ran and circulation was bad. Also it says it has air conditioning but that is only 1 room. We had a family of four and had to time out...
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    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean-view 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? Relax...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Ipswich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Secure Parking
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This well appointed home sits on a Hill overlooking plum Island sound with water access across the street. 10 minute walk to a Sandy private beach. A gated Wrap around deck is easily locked. Open airy light filled floor plan throughout makes this the perfect vacation spot to enjoy the water views....
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    Location Information
    Ipswich, Massachusetts 01938
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Granite Pier, with its unparalleled ocean views, is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Quarry Crest House: Includes swimming rights to Little Parker quarry1 / 29
    (1)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 22, 2017
    We had a really nice vacation staying at Quarry Crest House in Rockport with our daughter, son-in-law and 23-month old grandson for nine days. The house was perfect for us with...
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    About this property
    Enjoy the best of all worlds in this spacious and bright vacation rental home overlooking Rockport's stunningly picturesque Flat Ledge Quarry. Not only can you walk to town or to the beach in a few minutes, but the property includes full deeded swimming rights to Little Parker Quarry – a second...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    • Cable/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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Rockport
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location—that’s Rockport's sought-after South End. Find yourself just a minute's walk to the Atlantic Ocean for a swim at Old Garden Beach or take in the coastal view featuring Rockport's twin lighthouses on historic Thatcher Island. Inside this renovated ranch-style vacation...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Captain's Cottage: Traditional setting with a private footbridge to the beach1 / 16
    (1)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2016
    We stayed here for a week and Loved it!! It's soo private and quite the only thing we could hear at night were the crickets and crashing waves of the Atlantic! The Captain's...
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    About this property
    This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the traditional summer cottage...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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