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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
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4.96 out of 5 average rating, 306 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top 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
15–20 Aug
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Cabin in Rockport
The Solar Powered Dogtown Cabin at Applecart Farm
4.97 out of 5 average rating, 495 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.92 out of 5 average rating, 12 reviews, 2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 137 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
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
Guest favourite
Home in Gloucester
The Essex of Gloucester
4.96 out of 5 average rating, 82 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
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
13–18 Jul
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Gloucester
Private Beach!
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Room in Gloucester
Suite Magnolia
5.0 out of 5 average rating, 57 reviews, 1 king bed, 1 bathroom
9–14 Jul
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 217 reviews, 4 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Rockport
Sea Vagabond - Watch the waves, stroll to the sand
4.81 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
4.98 out of 5 average rating, 749 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug