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Search results; Over 1,000 homes in Gloucester

Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 private bathroom
30 Oct – 4 Nov
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4.86 out of 5 average rating, 138 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 87 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.92 out of 5 average rating, 36 reviews
Guest favourite
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 89 reviews
Guest favourite
Flat in Beverly
Cozy Boho Den
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Gloucester
House on tidal river, spacious deck, private yard
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed, 1 bathroom
4–9 Apr
4.92 out of 5 average rating, 249 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 281 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
4–9 Dec
4.98 out of 5 average rating, 178 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Rockport
Waterfront Condo/Heart Of Rockport/Bearskin Neck
1 bedroom, 2 beds, 1 bathroom
21–26 Nov
5.0 out of 5 average rating, 11 reviews
Superhost
Flat in Gloucester
Stay at the Marina
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Rockport
The Solar Powered Dogtown Cabin at Applecart Farm
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 497 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 88 reviews