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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds, 3 private bathrooms
31 Aug – 5 Sept
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4.98 out of 5 average rating, 48 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, 81 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, 42 reviews
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
1 bedroom, 1 queen bed, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 87 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
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
4.92 out of 5 average rating, 36 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Superhost
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds, 1.5 bathrooms
8–13 Aug
New place to stay
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, 9 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.85 out of 5 average rating, 221 reviews
Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 114 reviews
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
7–12 Aug
New place to stay
Guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Townhouse in Gloucester
Between 2 Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 198 reviews
Guest favourite
Flat in Gloucester
Folly Cove Waterside
2 bedrooms, 2 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds, 1 bathroom
26–31 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 71 reviews