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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
4–9 Apr
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4.92 out of 5 average rating, 255 reviews
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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
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Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 44 reviews
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Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
New place to stay
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Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 21 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, 31 reviews
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Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 bathrooms
3–10 Nov
4.99 out of 5 average rating, 74 reviews
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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
5 bedrooms, 10 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 64 reviews
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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, 31 reviews
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Top guest favourite
Home in Gloucester
Stay at The Neck
3 bedrooms, 4 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
9–14 Sept
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Home in Gloucester
House on tidal river, spacious deck, private yard
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 118 reviews
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Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.9 out of 5 average rating, 40 reviews
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Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 64 reviews