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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
,
4.92 out of 5 average rating, 257 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
14–19 Sept
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Home in Gloucester
4 plus bedrms 5 baths- 3 level Beachfront House.
4 bedrooms, 8 beds
14–19 Sept
4.99 out of 5 average rating, 70 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
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
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds
13–18 Sept
4.99 out of 5 average rating, 94 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
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
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds
13–18 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 375 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, 62 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
1–6 Oct
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 31 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Gloucester
Stay at Smith Cove
2 bedrooms, 3 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 reviews
Guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds
16–21 Sept
4.94 out of 5 average rating, 16 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
Townhouse in Gloucester
Between 2 Beaches
3 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 201 reviews