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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Aug
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4.97 out of 5 average rating, 151 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 78 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 140 reviews, 5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
5.0 out of 5 average rating, 31 reviews, 4 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Parsons at Stage Fort
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Guest favourite
Home in Gloucester
Private Beachfront Property in Gloucester
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Nov
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Gloucester
Lovely home by the sea!
4.95 out of 5 average rating, 19 reviews, 3 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
Superhost
Home in Gloucester
Stay at Wingaersheek
New place to stay, 3 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
4.9 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Sept
Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
Top guest favourite
Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
4.97 out of 5 average rating, 70 reviews, 10 bedrooms, 15 beds, 3 bathrooms
16–22 Aug
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
4.95 out of 5 average rating, 41 reviews, 3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4.99 out of 5 average rating, 221 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
Superhost
Home in Gloucester
Stay at Good Harbor Beach
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 219 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug