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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Premium Large Modern 2-Acre Retreat *Video Tour*
4 bedrooms, 7 beds, 3 private bathrooms
15–22 Aug
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4.96 out of 5 average rating, 23 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, 76 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, 40 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 26 reviews
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 82 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, 139 reviews
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Jul
4.99 out of 5 average rating, 221 reviews
Superhost
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 158 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
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, 94 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 41 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
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
24–30 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 36 reviews
Cabin in Beverly
Garden School Cabin
2 beds, 1 bathroom
1–6 Nov
New place to stay