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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 143 reviews
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 152 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
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Sept
4.93 out of 5 average rating, 46 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, 73 reviews
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
7–12 Nov
4.98 out of 5 average rating, 759 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 373 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, 24 reviews
Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
10–15 Sept
4.94 out of 5 average rating, 16 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
Superhost
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Nov
4.99 out of 5 average rating, 86 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, 34 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
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, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 64 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
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, 41 reviews
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 65 reviews