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Cape Ann Luxury Holiday Rentals

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    Travellers to Cape Ann are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    21 Matching Rentals in Cape AnnView all 141 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Wi-Fi
    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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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious vacation rental home is situated on the highest point of Brier Neck with astounding ocean views from every angle. Ascend the outside steps of this Tudor-style home and observe the rolling lawn on one side and take in the spectacular 240 degree views (and sounds of the surf) of...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Annisquam, Grandview is a stately and gracious vacation home in a private and lushly landscaped setting. Atop a hill, the property commands incredible views of both the Annisquam River and of the sea. Grandview is timelessly elegant and comfortable, with plenty of space for...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Golden Sands is the quintessential turn of the century Gloucester beach 'cottage.' With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house. The main level includes...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate up to 16 people, making it the perfect getaway for family reunions or vacations with friends. The house was completely refurbished and refreshed in 2017. Inside, a one-of-a-kind...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The John Gott house is a magnificently restored antique Colonial residence that pairs authentic Americana with the sophistication of modern living. Built in 1806, this historic home lets you step back in time to a bygone era and participate in a true New England experience. Built by a master then...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Booth Cottage Ocean view, private path to beach. Private mowed path, ten minute walk to village, harbor, 2 parks, on the commuter rail, four bedrooms, three full and one 1/2 bath, extra large lawn for ball playing, large porches, high ceilings, large windows. 3000$ per week, lower rates off...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy the views of the sunrise. On a clear day,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
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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 30 August 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 7 August 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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Tower at Marmion: Steps away from Old Garden Beach.1 / 30
    (1)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    First the good parts: There’s a beautiful back patio, with nice furniture and grill, and huuuuge level backyard in a great location; quiet and peaceful but close enough to walk...
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    About this property
    Experience a true Rockport getaway just a few minute's walk from the Atlantic Ocean and Old Garden Beach. Tower at Marmion is an elegant, gracious and spacious vacation rental home in Rockport's desirable South End. It is a charming property with lots of history, a formal dining room with French...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful house your home base for your beach escape this summer. The main level of the home consists of the gracious and architecturally stunning sun...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    Suitability
    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
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the 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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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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