
Vacation rentals in Thimble Islands
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Top-rated vacation rentals in Thimble Islands
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Thimble Islands vacation rentals
Other great vacation rentals in Thimble Islands
Guest favorite

Cottage in Branford
5 out of 5 average rating, 13 reviewsBeachfront Cottage Serene Private Beach, Kayaks
Guest favorite

Home in Madison
4.85 out of 5 average rating, 40 reviewsCozy beach cottage close to everthing
Superhost

Home in Branford
4.86 out of 5 average rating, 14 reviewsCalm Private Beach | less than 2h from NYC
Top guest favorite

Barn in Deep River
5 out of 5 average rating, 20 reviewsSalt House
Top guest favorite

Guesthouse in Madison
4.97 out of 5 average rating, 78 reviewsThe Barn by the Sound
Guest favorite

Tiny home in East Lyme
4.99 out of 5 average rating, 70 reviewsLakeside Serenity Tiny House
Superhost

Home in Guilford
4.73 out of 5 average rating, 142 reviewsPurple Button Factory Sleeps 6 Walk to Town Green
Guest favorite

Home in Mattituck
4.92 out of 5 average rating, 91 reviewsModern farmhouse w/ pool, beach, horses and winery
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- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
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- Shinnecock Hills Golf Club
- TPC River Highlands
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