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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 private bathrooms
10–17 Oct
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4.99 out of 5 average rating, 70 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 78 reviews
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
New place to stay
Guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 95 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
26–31 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Home in Gloucester
Private Beach!
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.94 out of 5 average rating, 77 reviews
Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.84 out of 5 average rating, 219 reviews
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
26–31 Aug
4.99 out of 5 average rating, 221 reviews