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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Waterfront Rocky Neck Cottage | Gloucester Harbor
3 bedrooms, 4 beds, 1 private bathroom
3–8 Nov
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4.93 out of 5 average rating, 193 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
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
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 140 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
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
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds
19–24 Sept
4.8 out of 5 average rating, 282 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
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
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 104 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
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds
3–8 Nov
4.97 out of 5 average rating, 76 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
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds
15–20 Nov
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds
4–9 Oct
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
1–6 Oct
4.94 out of 5 average rating, 47 reviews