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Search results; Over 1,000 homes in Gloucester

Guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds, 1 private bathroom
3–8 Nov
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4.95 out of 5 average rating, 232 reviews
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
4.94 out of 5 average rating, 16 reviews
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
12–17 Nov
5.0 out of 5 average rating, 24 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, 94 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Book Your Next Getaway Today!
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 85 reviews
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 bathrooms
3–10 Nov
4.99 out of 5 average rating, 75 reviews
Top guest favourite
Home in Gloucester
Stay at Smith Cove
2 bedrooms, 3 queen beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Rockport
Artist Cottage: A Rockport Retreat.
1 bedroom, 1 double bed, 1 bathroom
6–11 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 118 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 373 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, 110 reviews
Top guest favourite
Home in Rockport
Walk to Beach & Shops at Historic Renovation
3 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.98 out of 5 average rating, 127 reviews