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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Premium Large Modern 2-Acre Retreat *Video Tour*
4 bedrooms, 7 beds, 3 private bathrooms
15–22 Aug
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4.96 out of 5 average rating, 23 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
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
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 76 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
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
Superhost
Home in Gloucester
Stay at Good Harbor Beach
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
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
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
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
Top guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
4.99 out of 5 average rating, 94 reviews, 3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
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
3–8 Aug
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–30 Aug
Cabin in Beverly
Garden School Cabin
New place to stay, 2 beds, 1 bathroom
1–6 Nov
Guest favourite
Home in Gloucester
Private Beachfront Property in Gloucester
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Nov
Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
4.99 out of 5 average rating, 70 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–17 Oct
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
4.96 out of 5 average rating, 223 reviews, 1 bedroom, 3 beds, 1 bathroom
4–9 Sept
Top guest favourite
Room in Gloucester
Suite Magnolia
5.0 out of 5 average rating, 59 reviews, 1 king bed, 1 bathroom
2–7 Aug
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