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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
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
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.99 out of 5 average rating, 135 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
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, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 7 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
New place to stay
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
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, 1 bathroom
10–15 Jul
4.94 out of 5 average rating, 77 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 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, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 17 reviews
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Gloucester
Pavilion Beach Townhouse
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Flat in Rockport
4 Bed Water View w/ Parking
4 bedrooms, 5 beds, 2 bathrooms
10–15 Nov
4.99 out of 5 average rating, 167 reviews
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 76 reviews
Flat in Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.87 out of 5 average rating, 167 reviews
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
3–8 Aug
4.98 out of 5 average rating, 748 reviews