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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Annisquam
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
,
4.96 out of 5 average rating, 304 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
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
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
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
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 38 reviews, 4 bedrooms, 7 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 169 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
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
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 135 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
5.0 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1 bathroom
4–9 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
Flat in Gloucester
Artist Retreat
4.92 out of 5 average rating, 24 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 119 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Flat in Gloucester
Ocean View | Walk to Downtown & Beach | Skylight
4.98 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Cottage in Gloucester
Shore Cottage • Peaceful Coastal Retreat
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul