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Search results; Over 1,000 homes in Gloucester

Descriptions are based on details hosts provide
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
17–22 Oct
,
4.92 out of 5 average rating, 243 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Gloucester
Waterfront home with a deck and fire pit
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Clawfoot tub with cove views, gas fireplace
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 39 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
Guest favourite
Flat in Gloucester
Newly renovated, blocks from the beach
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
Cabin in Beverly
Historic cottage on a forested garden knoll
New place to stay, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Home in Gloucester
Renovated, walk to marina and beach
4.99 out of 5 average rating, 138 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
4.99 out of 5 average rating, 82 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 219 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
4.98 out of 5 average rating, 750 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Townhouse in Gloucester
Ocean-facing porch with rockers on the waterfront
4.94 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Home in Gloucester
Harbor views from the sunroom and deck
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
5.0 out of 5 average rating, 31 reviews, 4 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
Superhost
Home in Gloucester
Waterfront on Wonson’s Cove in Rocky Neck
New place to stay, 4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
Guest favourite
Flat in Gloucester
Remodeled in 2022, 2 blocks from Main
4.96 out of 5 average rating, 150 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Oct