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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 private bathroom
6–11 Nov
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4.92 out of 5 average rating, 118 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.97 out of 5 average rating, 149 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
2–7 Nov
4.98 out of 5 average rating, 99 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds
2–7 Nov
4.97 out of 5 average rating, 35 reviews
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Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds
3–8 Nov
4.98 out of 5 average rating, 113 reviews
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds
12–17 Sept
4.8 out of 5 average rating, 281 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 110 reviews
Top guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
2–7 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
12–17 Sept
4.96 out of 5 average rating, 45 reviews
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Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds
8–13 Nov
4.93 out of 5 average rating, 46 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds
2–7 Nov
4.96 out of 5 average rating, 160 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds
15–20 Nov
4.9 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 60 reviews
Guest favourite
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Gloucester
Chic Gloucester Escape•Harbor&Dining•Close2Salem
1 bedroom, 1 queen bed
13–18 Sept
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Gloucester
Panoramic Ocean View; walk to private beach
5 bedrooms, 8 beds
1–6 Oct
4.97 out of 5 average rating, 90 reviews