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

Cottage in Guilford
4.95 out of 5 average rating, 82 reviewsDirect Shoreline Long Island Sound Waterfront
Top guest favourite

Tiny home in East Lyme
4.98 out of 5 average rating, 56 reviewsLakeside Serenity Tiny House

Home in Guilford
4.92 out of 5 average rating, 12 reviewsWaterfront Home With Private Beach & Tennis Court
Guest favourite

Cottage in Branford
4.97 out of 5 average rating, 73 reviewsOcean view cottage in Indian Neck
Top guest favourite

Cottage in Greenport
5 out of 5 average rating, 22 reviewsCoastal Cottage | Near Beach & Town | Baby Gear
Guest favourite

Home in Wading River
5 out of 5 average rating, 19 reviewsHang by the (Chel)SEA
Superhost

Cottage in Branford
4.83 out of 5 average rating, 6 reviewsBeachside Branford- walk to Beach, Grill
Top guest favourite

Tiny home in Guilford
4.98 out of 5 average rating, 87 reviewsSeagrass Bungalow
Destinations to explore
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- Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Ocean Beach Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Thunder Ridge Ski Area
- Silver Sands Beach
- Amagansett Beach
- Groton Long Point Main Beach
- Bushnell Park
- Sunken Meadow State Park
- Seaside Beach
- South Jamesport Beach
- Sandy Beach
- Sherwood Island State Park
- Calf Pasture Beach