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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Plum Cove Cottage with king suite!
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
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4.93 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 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
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 39 reviews, 4 bedrooms, 7 beds, 3 bathrooms
15–20 Aug
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
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 6 beds, 1 bathroom
23–28 Aug
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
4.94 out of 5 average rating, 31 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 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
Guest favourite
Flat in Gloucester
Artist Retreat
4.92 out of 5 average rating, 24 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 170 reviews, 3 bedrooms, 3 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, 136 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
4.97 out of 5 average rating, 88 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
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
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
5.0 out of 5 average rating, 84 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
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
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
4.91 out of 5 average rating, 76 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul