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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
11–16 Nov
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4.97 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 26 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, 99 reviews
Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds
3–8 Nov
4.97 out of 5 average rating, 76 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
11–16 Sept
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds
13–18 Nov
4.99 out of 5 average rating, 88 reviews
Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Gloucester
Stay at Smith Cove
2 bedrooms, 3 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 138 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds
13–18 Sept
4.97 out of 5 average rating, 373 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, 35 reviews
Guest favourite
Home in Gloucester
Luxury Townhouse in Downtown with Free Parking #2
3 bedrooms, 3 beds
16–21 Nov
4.94 out of 5 average rating, 89 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds
25–30 Oct
4.98 out of 5 average rating, 60 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
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
12–17 Sept
4.96 out of 5 average rating, 45 reviews