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Search results; Over 1,000 homes in Gloucester

Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 private bathroom
2–7 Nov
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4.86 out of 5 average rating, 138 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
4.96 out of 5 average rating, 45 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
Home in Gloucester
Stay at Rocky Neck
3 bedrooms, 3 queen beds, 2.5 bathrooms
16–21 Oct
4.96 out of 5 average rating, 26 reviews
Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Gloucester
4 plus bedrms 5 baths- 3 level Beachfront House.
4 bedrooms, 8 beds, 5 bathrooms
23–28 Sept
4.99 out of 5 average rating, 70 reviews
Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.93 out of 5 average rating, 14 reviews
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, 31 reviews
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 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
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 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
Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.96 out of 5 average rating, 152 reviews
Top guest favourite
Flat in Gloucester
Cozy Apartment at Green Landing, No Cleaning Fee
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Nov
4.99 out of 5 average rating, 86 reviews