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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
4–9 Apr
,
4.92 out of 5 average rating, 248 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 81 reviews
Home in Essex
Home in Essex
2 bedrooms, 2 queen beds
18–23 Aug
New place to stay
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
8–13 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 154 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Gloucester
Lovely home by the sea!
3 bedrooms, 7 beds
8–13 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds
8–13 Nov
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 97 reviews
Top guest favourite
Home in Gloucester
The Beach House on the Boulevard Ocean Front!
5 bedrooms, 18 beds
24–29 Aug
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 33 reviews