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Search results; Over 1,000 homes in Gloucester

Guest favourite
Home in Gloucester
Walk To Good Harbor, OCEAN VIEWS, Open All Year!
3 bedrooms, 4 beds, 2 private bathrooms
5–10 Sept
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4.86 out of 5 average rating, 66 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 284 reviews
Top guest favourite
Room in Ipswich
Cedarwood Farm - Marie Antoinette Suite
1 queen bed, 1 bathroom
18–23 Aug
4.96 out of 5 average rating, 46 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 12 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, 37 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Guest suite in Gloucester
The Artist Suite by Toi Moi
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 81 reviews
Superhost
Flat in Gloucester
Stay at the Marina (Gloucester)
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 757 reviews
Top guest favourite
Home in Rockport
Pleasant Place Parking • Walk to Downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 126 reviews
Top guest favourite
Guest suite in Newbury
Parker River House Two Bedroom
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 93 reviews
Guest favourite
Flat in Beverly
Cozy Boho Den
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 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, 24 reviews
Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 156 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Rockport
Rockport Studio w/parking|Walk 2 Downtown Rockport
1 queen bed, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 85 reviews