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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
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4.96 out of 5 average rating, 306 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, 137 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 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
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds
30 Aug – 4 Sept
4.92 out of 5 average rating, 12 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
12–17 Sept
New place to stay
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 75 reviews
Guest favourite
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, 5 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
20–25 Jul
5.0 out of 5 average rating, 22 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, 171 reviews
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Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds
8–13 Sept
4.94 out of 5 average rating, 18 reviews
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed
23–28 Aug
5.0 out of 5 average rating, 3 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
Flat in Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
1 bedroom, 2 beds
26–31 Jul
4.86 out of 5 average rating, 168 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds
12–17 Jul
4.88 out of 5 average rating, 140 reviews
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
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Tiny home in Gloucester
Smith Cove Cottgage
1 bedroom, 2 beds
9–14 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
2 bedrooms, 4 beds
16–21 Nov
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds
29 Aug – 3 Sept
4.95 out of 5 average rating, 40 reviews