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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 shared bathroom
11–16 Nov
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4.99 out of 5 average rating, 88 reviews
Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Gloucester
4 plus bedrms 5 baths- 3 level Beachfront House.
4 bedrooms, 8 beds, 5 bathrooms
14–19 Sept
4.99 out of 5 average rating, 70 reviews
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
16–21 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 376 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 27 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, 139 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, 62 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
Guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.91 out of 5 average rating, 289 reviews
Guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds, 1 bathroom
3–8 Nov
4.95 out of 5 average rating, 233 reviews
Top guest favourite
Home in Gloucester
Stay at Rocky Neck
3 bedrooms, 3 queen beds, 2.5 bathrooms
14–19 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Gloucester
Cozy Apartment at Green Landing, No Cleaning Fee
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Home in Rockport
Pleasant Place Parking • Walk to Downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 130 reviews
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Rockport
Artist Cottage: A Rockport Retreat.
1 bedroom, 1 double bed, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Gloucester
Stay at Smith Cove
2 bedrooms, 3 queen beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 reviews