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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 142 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.97 out of 5 average rating, 146 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
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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, 43 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, 29 reviews
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Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Home in Annisquam
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
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Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.9 out of 5 average rating, 10 reviews
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Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 133 reviews
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Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 59 reviews
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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, 38 reviews
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Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 12 reviews
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Flat in Gloucester
East Gloucester Beach house
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 77 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, 111 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, 46 reviews