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Search results; Over 1,000 homes in Gloucester

Guest favourite
Room in Gloucester
Harborview Inn
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.83 out of 5 average rating, 18 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, 98 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
Gloucester Ocean View Home
4 bedrooms, 7 beds
11–16 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
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
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
11–16 Sept
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 30 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, 33 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, 24 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
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds
13–18 Nov
4.99 out of 5 average rating, 86 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds
14–19 Sept
4.97 out of 5 average rating, 65 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
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds
9–14 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Gloucester
House on tidal river, spacious deck, private yard
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Gloucester
Stay at Rocky Neck
3 bedrooms, 3 queen beds
13–18 Sept
4.96 out of 5 average rating, 26 reviews