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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
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4.96 out of 5 average rating, 307 reviews
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
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
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
12–17 Jul
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.92 out of 5 average rating, 12 reviews, 2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
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
Blue Magnolia
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 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
20–25 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
13–18 Jul
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 217 reviews, 4 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 275 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Tiny home in Gloucester
Smith Cove Cottgage
5.0 out of 5 average rating, 24 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 172 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
4.91 out of 5 average rating, 78 reviews, 2 bedrooms, 3 beds, 1 bathroom
4–9 Aug
Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
4.91 out of 5 average rating, 111 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
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
Guest favourite
Flat in Rockport
Long Beach Suites: Steps Away From Surf!
4.88 out of 5 average rating, 140 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov