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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Cottage in Gloucester
SeaHaven Cottage at Stage Fort Park
2 bedrooms, 2 beds, 2 private bathrooms
12–17 Sept
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4.86 out of 5 average rating, 191 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, 46 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
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
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
29 Sept – 4 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, 3 bathrooms
12–17 Sept
4.96 out of 5 average rating, 45 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
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
Stay at Smith Cove
2 bedrooms, 3 queen beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 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
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 Gloucester
Stay at Rocky Neck
3 bedrooms, 3 queen beds, 2.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Gloucester
Stay at the Marina
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Gloucester
4 plus bedrms 5 baths- 3 level Beachfront House.
4 bedrooms, 8 beds, 5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 70 reviews
Guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.94 out of 5 average rating, 16 reviews