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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Cottage in Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
4 bedrooms, 6 beds, 2 private bathrooms
4–9 Oct
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4.86 out of 5 average rating, 192 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
17–22 Sept
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 reviews
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Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 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
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 94 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, 27 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
29 Sept – 4 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Flat in Gloucester
Cozy Apartment at Green Landing, No Cleaning Fee
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Home in Gloucester
Stay at Rocky Neck
3 bedrooms, 3 queen beds, 2.5 bathrooms
1–6 Nov
4.96 out of 5 average rating, 26 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, 32 reviews
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Loft in Gloucester
Gloucester Large 2-Room Studio, Full Kitchen, Deck
1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 6 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
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 140 reviews
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Guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 67 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
25–30 Oct
4.98 out of 5 average rating, 60 reviews
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 reviews
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Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.96 out of 5 average rating, 152 reviews