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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Flat in Gloucester
The Gilbert: 1-Bed downtown suite, walk to beach.
1 bedroom, 1 bed, 1 private bathroom
1–6 Mar
,
4.96 out of 5 average rating, 192 reviews
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Featured hotel
Hotel in Gloucester
Ocean House Hotel at Bass Rocks, Deluxe two queen.
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
New place to stay
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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
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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, 29 reviews
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.91 out of 5 average rating, 53 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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Superhost
Home in Gloucester
Cranberry Hill | 9 BR 22 Acre Estate | Sleeps 22
9 bedrooms, 13 beds, 6.5 bathrooms
10–15 Oct
4.87 out of 5 average rating, 23 reviews
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Top guest favourite
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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Top guest favourite
Flat in Gloucester
Stay at the Marina
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.94 out of 5 average rating, 47 reviews
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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, 115 reviews
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Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 152 reviews
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Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
10 bedrooms, 15 beds, 3 bathrooms
1–7 Oct
4.97 out of 5 average rating, 75 reviews
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Guest favourite
Flat in Gloucester
New Design•Walk2DNTN•Beach•Train•Close to Salem
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 120 reviews
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Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.98 out of 5 average rating, 766 reviews