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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds, 2 private bathrooms
25–30 Oct
,
4.99 out of 5 average rating, 164 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
17–22 Nov
4.97 out of 5 average rating, 147 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
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 41 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
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.94 out of 5 average rating, 79 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
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 92 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
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
2 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.97 out of 5 average rating, 158 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
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 135 reviews
Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 103 reviews
Guest favourite
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 94 reviews
Guest favourite
Flat in Gloucester
East Gloucester Beach house
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Rockport
Folly Cove Waterside
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 8 reviews