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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Flat in Gloucester
Ocean and Woods! Best of both in Gloucester!
2 bedrooms, 3 beds, 1 private bathroom
4–9 Nov
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5.0 out of 5 average rating, 39 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 76 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 40 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 139 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Superhost
Home in Rockport
Waterfront Retreat at Motif Annex
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 81 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
4.94 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Flat in Manchester-by-the-Sea
New Listing: Manchester-by-the-Sea Retreat
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
4.98 out of 5 average rating, 57 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
4.98 out of 5 average rating, 136 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Tiny home in Gloucester
Smith Cove Cottgage
5.0 out of 5 average rating, 27 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Sept
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
4.97 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
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