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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 private bathrooms
10–17 Oct
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4.99 out of 5 average rating, 70 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 39 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Gloucester
Stay at Gloucester Harbor
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.91 out of 5 average rating, 34 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in Gloucester
Lovely home by the sea!
3 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.99 out of 5 average rating, 93 reviews