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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, 244 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 76 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
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, 40 reviews
Superhost
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
New place to stay
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
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 81 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, 32 reviews
Guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds, 1 bathroom
26–31 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Apartment in Gloucester
KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Aug
4.96 out of 5 average rating, 195 reviews
Flat in Manchester-by-the-Sea
New Listing: Manchester-by-the-Sea Retreat
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
3 bedrooms, 3 queen beds, 2 bathrooms
3–8 Oct
4.97 out of 5 average rating, 89 reviews
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 136 reviews
Guest favourite
Tiny home in Gloucester
Smith Cove Cottgage
1 bedroom, 2 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 83 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 151 reviews