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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
6–11 Dec
4.97 out of 5 average rating, 148 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
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds
20–25 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
“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
Guest favourite
Flat in Gloucester
Stay at the Marina (Gloucester)
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 9 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
Home in Annisquam
Hide & Seek
4 bedrooms, 7 beds
14–19 Sept
New place to stay
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
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
Top guest favourite
Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds
15–20 Nov
4.92 out of 5 average rating, 118 reviews
Top guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
2–7 Nov
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds
14–19 Sept
4.97 out of 5 average rating, 64 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
Top guest favourite
Home in Annisquam
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 58 reviews