Winter Vacation Rentals & Cabin Rentals in Gloucester, MA

Compare 944 available beachfront holiday vacation home properties, starts from $16

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Gloucester, MA: Top Deals

The Cove at Rockport
The Cove at Rockport
The Cove at Rockport
The Cove at Rockport
The Cove at Rockport
The Cove at Rockport
The Cove at Rockport
4.5 (64 reviews)
The Cove at Rockport
Hotel
$134 /night
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The Beech Tree B&B
The Beech Tree B&B
The Beech Tree B&B
The Beech Tree B&B
The Beech Tree B&B
The Beech Tree B&B
The Beech Tree B&B
5.0 (6 reviews)
The Beech Tree B&B
Hotel
$235 /night
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Julietta House
Julietta House
Julietta House
Julietta House
Julietta House
Julietta House
Julietta House
Julietta House
4.7 (33 reviews)
Julietta House
House
$180 /night
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Vintage Rockport Escape
Vintage Rockport Escape
Vintage Rockport Escape
Vintage Rockport Escape
Vintage Rockport Escape
Vintage Rockport Escape
Vintage Rockport Escape
4.7 (14 reviews)
Vintage Rockport Escape
Hotel
$120 /night
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The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
The Quarterdeck Inn by the Sea
4.4 (86 reviews)
The Quarterdeck Inn by the Sea
Hotel
$239 /night
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Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
4.9 (73 reviews)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Studio · 4 Guests · 1 Bedroom
$150 /night*
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Eagle House Motel
Eagle House Motel
Eagle House Motel
Eagle House Motel
Eagle House Motel
Eagle House Motel
Eagle House Motel
4.3 (84 reviews)
Eagle House Motel
House
$130 /night
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Yankee Clipper Inn
Yankee Clipper Inn
Yankee Clipper Inn
Yankee Clipper Inn
Yankee Clipper Inn
Yankee Clipper Inn
Yankee Clipper Inn
4.4 (112 reviews)
Yankee Clipper Inn
Hotel
$159 /night
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The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
The Hotel Marblehead
4.5 (62 reviews)
The Hotel Marblehead
Hotel
$189 /night
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Similar Inspirational Vacation Rental Destinations

How Does The Vacation Home Rental Price Look Like in Gloucester, MA?
Vacation House & Cottage Rental Price Information in Gloucester, MA
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The graph shows the percentages of vacation homes in each price bucket. Gloucester has the largest percentage (16.45%) of homes in $150 - $200 price range.
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What are the best places for snowbirds to visit in Gloucester, MA?
Places of Interest for Snowbirds in Gloucester, MA
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Gloucester, MA is an excellent destination for snowbirds. With its stunning coastal scenery and proximity to Boston, this city offers a great variety of activities suitable for seniors. It has a mild climate throughout the year, with temperatures rarely dropping below freezing in the winter months. The community is filled with friendly people who are welcoming to visitors, and there are plenty of restaurants, shops and attractions to keep you busy. Healthcare facilities are easily accessible should any medical needs arise.

  • Cape Ann Museum

    The Cape Ann Museum houses a collection of artwork related to the local area, including pieces by Winslow Homer and Fitz Henry Lane. It provides an interesting insight into the history of Gloucester and is a great place to spend an afternoon. Wheelchair access is available, and the museum also has a cafe and gift shop.

  • Ravenswood Park

    Ravenswood Park is situated on the edge of the Annisquam River and offers a range of recreational activities. There are walking trails, picnic areas and fishing spots, making it perfect for those looking for some fresh air and outdoor exercise. The park is wheelchair-accessible and open all year round.

  • Good Harbor Beach

    Good Harbor Beach is a popular spot for swimming, sunbathing and beachcombing. The beach has a gentle slope which makes it easy to access from the parking lot. There are accessible restrooms and showers, and lifeguards are on duty during the summer season. Visitors can enjoy panoramic views of the Atlantic Ocean from here.

How Many Accommodations Are Not Pets Friendly in Gloucester, MA?
Pets Allowed vs Not Allowed in Gloucester, MA
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27.12% of vacation homes in Gloucester are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Best Tourist Attractions in Gloucester, MA?
Destinations To Visit During the Winter in Gloucester, MA
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Which Airports Should I Choose To Get To Gloucester, MA?
Suggested Airports in Gloucester, MA
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