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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 private bathrooms
21–26 Sept
,
4.96 out of 5 average rating, 152 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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Top guest favourite
Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed, 1 bathroom
1–6 Nov
4.87 out of 5 average rating, 46 reviews
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Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 110 reviews
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Top guest favourite
Apartment in Rockport
Widows Bay Rockport Apt • Train To Salem
1 bedroom, 3 beds, 1 bathroom
9–14 Oct
4.95 out of 5 average rating, 130 reviews
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Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
20–25 Nov
4.99 out of 5 average rating, 93 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 reviews
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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, 28 reviews
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Top guest favourite
Guest house in Rockport
Historic Carriage House | Dog Friendly | Hot Tub
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 175 reviews
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Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
11–16 Nov
4.99 out of 5 average rating, 89 reviews
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Top guest favourite
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 65 reviews
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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, 99 reviews
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Top guest favourite
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
3–8 Nov
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
12–17 Oct
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 43 reviews
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Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 bathrooms
3–8 Nov
4.97 out of 5 average rating, 77 reviews
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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