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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
3–8 Nov
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4.93 out of 5 average rating, 191 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.97 out of 5 average rating, 149 reviews
Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds, 2.5 bathrooms
3–8 Nov
4.98 out of 5 average rating, 112 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Nov
4.98 out of 5 average rating, 98 reviews
Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 103 reviews
Top guest favourite
Home in Gloucester
Pavilion Beach Townhouse
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Sept
4.8 out of 5 average rating, 281 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
4.96 out of 5 average rating, 48 reviews
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Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds, 2 bathrooms
10–15 Nov
4.99 out of 5 average rating, 164 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
4.96 out of 5 average rating, 45 reviews
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Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Nov
4.93 out of 5 average rating, 46 reviews
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, 287 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.9 out of 5 average rating, 41 reviews