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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
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
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
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
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
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
Cabin in Beverly
Garden School Cabin
New place to stay, 2 beds, 1 bathroom
1–6 Nov
Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
4.99 out of 5 average rating, 158 reviews, 3 bedrooms, 5 beds, 2 bathrooms
22–27 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
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
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
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4.99 out of 5 average rating, 221 reviews, 4 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 219 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
4.95 out of 5 average rating, 41 reviews, 3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
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