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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
18–23 Oct
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4.97 out of 5 average rating, 142 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 88 reviews
Home in Essex
Home in Essex
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 bathrooms
28 Oct – 4 Nov
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Rockport
4 Bed Water View w/ Parking
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 60 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, 109 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 39 reviews
Superhost
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 27 reviews
Loft in Gloucester
Gloucester Large 2-Room Studio, Full Kitchen, Deck
1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
17–22 Nov
4.97 out of 5 average rating, 145 reviews