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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
,
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
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
8–13 Sept
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
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
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.91 out of 5 average rating, 11 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
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
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 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
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
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
Private Beach!
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
4.99 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
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
Flat in Manchester-by-the-Sea
New Listing: Manchester-by-the-Sea Retreat
New place to stay, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
Guest favourite
Home in Gloucester
Brand new home minutes to the ocean
4.94 out of 5 average rating, 63 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 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