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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 74 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
15–20 Aug
4.95 out of 5 average rating, 39 reviews
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds
13–18 Jul
New place to stay
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds
18–23 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds
13–18 Sept
4.94 out of 5 average rating, 31 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds
10–15 Jul
4.94 out of 5 average rating, 77 reviews
Guest favourite
Flat in Gloucester
Artist Retreat
1 bedroom, 1 king bed
12–17 Jul
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.99 out of 5 average rating, 136 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
1 bedroom, 1 queen bed
15–20 Jul
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
3 bedrooms, 3 queen beds
16–21 Sept
4.97 out of 5 average rating, 88 reviews
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4 bedrooms, 5 beds
12–17 Jul
4.84 out of 5 average rating, 217 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
13–18 Jul
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Gloucester
Private Beach!
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.96 out of 5 average rating, 53 reviews