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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Aug
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4.97 out of 5 average rating, 151 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 282 reviews
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
2 bedrooms, 2 beds, 1 bathroom
4–9 Dec
4.93 out of 5 average rating, 128 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
Guest favourite
Room in Ipswich
Cedarwood Farm - Marie Antoinette Suite
1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Guest suite in Newbury
Parker River House Two Bedroom
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 93 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 37 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.89 out of 5 average rating, 148 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, 250 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
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
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, 16 reviews
Superhost
Flat in Gloucester
Stay at the Marina (Gloucester)
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
11–16 Nov
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 757 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
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 21 reviews
Home in Essex
Home in Essex
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 367 reviews