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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
2 bedrooms, 3 beds, 1 private bathroom
18–23 Sept
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4.97 out of 5 average rating, 158 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.97 out of 5 average rating, 148 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds, 2.5 bathrooms
3–8 Nov
4.98 out of 5 average rating, 112 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Nov
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
12–17 Nov
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 286 reviews
Top guest favourite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Rockport
Sea Vagabond - Watch the waves, stroll to the sand
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.81 out of 5 average rating, 101 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.9 out of 5 average rating, 40 reviews
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
9–14 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 28 reviews
Guest favourite
Flat in Gloucester
Sunny 2 bedroom, close to beaches & harbor
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 32 reviews