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Search results; Over 1,000 homes in Gloucester

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, 257 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
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds
3–8 Nov
4.98 out of 5 average rating, 114 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 27 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
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 94 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
Guest favourite
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
16–21 Sept
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Gloucester
Pavilion Beach Townhouse
3 bedrooms, 3 beds
15–20 Sept
4.96 out of 5 average rating, 76 reviews
Top guest favourite
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
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds
1–6 Nov
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
10 bedrooms, 15 beds
15–21 Sept
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 140 reviews
Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds
16–21 Sept
5.0 out of 5 average rating, 3 reviews