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Search results; Over 1,000 homes in Gloucester

Guest favourite
Flat in Gloucester
Walk to Good Harbor Beach
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
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4.93 out of 5 average rating, 131 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 85 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 43 reviews
Superhost
Flat in Gloucester
Stay at the Marina (Gloucester)
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 88 reviews
Home in Essex
Home in Essex
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
18–23 Aug
New place to stay
Guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
17–22 Nov
4.97 out of 5 average rating, 144 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 37 reviews
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, 33 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Nov
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews
Guest favourite
Tiny home in Gloucester
Smith Cove Cottgage
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews