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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
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
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
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
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
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.92 out of 5 average rating, 37 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
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
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
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
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 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
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 29 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
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Gloucester
Ocean View | Walk to Downtown & Beach | Skylight
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.98 out of 5 average rating, 99 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.89 out of 5 average rating, 150 reviews