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Manchester-by-the-Sea Romantic Vacation Rentals

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    Don't let other travelers get your favorite Manchester-by-the-Sea area vacation rental. You're so close to securing your perfect getaway. Book today.
    12 Matching Rentals in the Manchester-by-the-Sea AreaView all 181 rentals
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    The following rentals are within 10 miles of Manchester-by-the-Sea.
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 27
    (17)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 25
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • 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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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meet Me on South Street is a charming condo in a 2 unit antique colonial building that is one of Rockport's finest examples of Early American architecture. Lovingly and painstakingly renovated, this two-bedroom getaway is tastefully furnished and comfortable. A sunny pied-à-terre, it is just the...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is close to walk to or short drive to restaurants and dining, family-friendly activities, the beach, nightlife, whale watching . You’ll love my place because of the coziness , the comfy bed, the relaxed and easy atmosphere, and close proximity to all Gloucester, Rockport and Cape Ann have...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
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    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming condominium is located on the ground floor of a coastal Victorian era complex. Overlooking Smith Cove and Gloucester Harbor, this romantic getaway is tastefully furnished, boasting a private patio where you can take in the views of the active port. Enter the property from the patio...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky...
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    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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, 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 residential street, this...
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    Location Information
    Rockport, Cape Ann 01966
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience old charm like never before in the idyllic North Eastern town of Rockport at this cozy vacation rental apartment. Shiplap walls, wide planked floors, and original exposed beams make this 1-bedroom, 1-bathroom home the perfect romantic getaway for 2. Walk out your front door and find...
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    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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