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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 king beds, 2 bathrooms
27 Aug – 1 Sept
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
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
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
Superhost
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 159 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
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
New place to stay
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
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.99 out of 5 average rating, 94 reviews
Guest favourite
Home in Gloucester
Private Beachfront Property in Gloucester
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 223 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
24–30 Aug
5.0 out of 5 average rating, 9 reviews
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 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
Smith Cove Cottage Condo
1 bedroom, 2 queen beds, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 52 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 39 reviews