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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
28 Aug – 2 Sept
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4.93 out of 5 average rating, 185 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 39 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, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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
18–23 Jul
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 138 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
4.99 out of 5 average rating, 156 reviews, 3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
5.0 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Guest suite in Gloucester
Herringbone Suite at Beacon House
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Nov
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
4.99 out of 5 average rating, 82 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 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
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
Flat in Gloucester
Folly Cove Waterside
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 3 Oct
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
13–18 Jul
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
5.0 out of 5 average rating, 84 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
4.9 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept