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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
17–22 Oct
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4.92 out of 5 average rating, 240 reviews
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
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
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
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
Guest suite in Gloucester
Herringbone Suite at Beacon House
New place to stay, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
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 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
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
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
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
Top guest favourite
Home in Gloucester
Pavilion Beach Townhouse
4.97 out of 5 average rating, 67 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
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
Flat in Gloucester
East Gloucester Beach house
4.89 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
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
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
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
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