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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 private bathrooms
11–16 Nov
,
4.97 out of 5 average rating, 143 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
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds
16–21 Nov
4.99 out of 5 average rating, 91 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, 112 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds
12–17 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
10 bedrooms, 15 beds
13–19 Sept
4.97 out of 5 average rating, 75 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
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
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
2–7 Nov
4.98 out of 5 average rating, 98 reviews
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds
12–17 Sept
4.8 out of 5 average rating, 281 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds
1–6 Nov
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds
15–20 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Gloucester
Beachside at GoodHarbor, King bed, fire pit, AC
5 bedrooms, 7 beds
12–17 Oct
4.91 out of 5 average rating, 68 reviews
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds
22–27 Sept
New place to stay
Superhost
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 6 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
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 60 reviews