filters

Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds, 2.5 private bathrooms
3–8 Nov
,
4.98 out of 5 average rating, 112 reviews
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, 26 reviews
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
Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
4.96 out of 5 average rating, 45 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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, 73 reviews
Guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 287 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 94 reviews
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
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 373 reviews
Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.95 out of 5 average rating, 44 reviews
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, 35 reviews
Top 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, 66 reviews
Guest favourite
Home in Gloucester
Luxury Townhouse in Downtown with Free Parking #2
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Nov
4.94 out of 5 average rating, 88 reviews
Guest favourite
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 5 reviews