Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Annisquam
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds, 3 private bathrooms
31 Aug – 5 Sept
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4.98 out of 5 average rating, 46 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
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
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
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
10–15 Jul
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
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
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Flat in Gloucester
Sunsets on the Seawall
New place to stay, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
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
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
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
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
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
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
4.89 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
4.91 out of 5 average rating, 76 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
4.97 out of 5 average rating, 149 reviews, 1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct