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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
17–22 Nov
4.97 out of 5 average rating, 147 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds
3–8 Sept
5.0 out of 5 average rating, 60 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, 98 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, 112 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds
16–21 Nov
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
12–17 Nov
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds
7–12 Sept
4.8 out of 5 average rating, 281 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 135 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, 33 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
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds
2–7 Nov
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Rockport
Sea Vagabond - Watch the waves, stroll to the sand
4 bedrooms, 5 beds
12–17 Sept
4.81 out of 5 average rating, 101 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 286 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds
6–11 Nov
4.9 out of 5 average rating, 40 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds
2–7 Nov
4.96 out of 5 average rating, 158 reviews
Guest favourite
Flat in Gloucester
The Gilbert: 1-Bed downtown suite, walk to beach.
1 bedroom, 1 king bed
1–6 Mar
4.97 out of 5 average rating, 188 reviews
Top guest favourite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 58 reviews