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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
28 Aug – 2 Sept
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4.93 out of 5 average rating, 183 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 bed
12–17 Sept
New place to stay
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
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
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, 135 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
10–15 Jul
5.0 out of 5 average rating, 7 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, 169 reviews
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
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
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed
30 Jul – 4 Aug
New place to stay
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 95 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, 21 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds
4–9 Jul
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds
2–7 Aug
4.94 out of 5 average rating, 16 reviews
Guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds
20–25 Jul
4.91 out of 5 average rating, 110 reviews
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
2 bedrooms, 2 beds
3–8 Oct
4.93 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds
6–11 Jul
5.0 out of 5 average rating, 23 reviews