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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 private bathrooms
8–13 Nov
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4.94 out of 5 average rating, 48 reviews
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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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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
3–8 Oct
4.9 out of 5 average rating, 51 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
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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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
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
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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Guest favourite
Home in Rockport
Classic New England: Big Family Home; Spas|Garden
10 bedrooms, 16 beds, 3.5 bathrooms
8–13 Nov
4.98 out of 5 average rating, 58 reviews
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Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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, 114 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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Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.86 out of 5 average rating, 138 reviews
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Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 59 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
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 33 reviews