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Search results; Over 1,000 homes in Gloucester

Guest favourite
Cottage in Gloucester
Cottage Oceanfront | Balcony | Dog Friendly | W/D
1 bedroom, 3 beds, 1.5 private bathrooms
8–13 Nov
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4.94 out of 5 average rating, 33 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.97 out of 5 average rating, 149 reviews
Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds
3–8 Nov
4.98 out of 5 average rating, 113 reviews
Guest favourite
Flat in Gloucester
East Gloucester Beach house
3 bedrooms, 4 beds
19–24 Sept
4.87 out of 5 average rating, 78 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
2–7 Nov
4.98 out of 5 average rating, 99 reviews
Guest favourite
Home in Gloucester
Luxury Townhouse in Downtown with Free Parking #2
3 bedrooms, 3 beds
16–21 Nov
4.94 out of 5 average rating, 89 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds
2–7 Nov
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds
1–6 Nov
4.96 out of 5 average rating, 96 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 110 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Home in Gloucester
Pavilion Beach Townhouse
3 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds
4–9 Oct
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
14–19 Sept
4.96 out of 5 average rating, 45 reviews