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Compare 300 Vacation Homes in Sheffield Island with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (6)

Captain's Cottage - Cold Spring Harbor Water Views
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (56)
The price is AED 727
AED 1,679 total
includes taxes & fees
9 Apr - 10 Apr

Business or Weekend escape
Business or Weekend escape
9.6 out of 10, Exceptional, (34)
The price is AED 275
AED 496 total
includes taxes & fees
7 Apr - 8 Apr

Cheerful 4 bedrooms residential house.
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (30)

Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (96)

Main Street Westport, walk to shops, dining, downtown
Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (28)

Over Sized Colonial on Private Road.
Over Sized Colonial on Private Road.
9.6 out of 10, Exceptional, (39)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Sheffield Island

DUNE Fairfield Beach
DUNE Fairfield Beach
8.8 out of 10, Excellent, (50)
The price is AED 834
AED 1,162 total
includes taxes & fees
14 Apr - 15 Apr

Stamford Suites
Stamford Suites
5.6 out of 10, (24)
The price is AED 630
AED 724 total
includes taxes & fees
20 Apr - 21 Apr

Global Luxury Suites White Plains
Global Luxury Suites White Plains
6.6 out of 10, (30)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Sheffield Island hotels
Recent reviews of Sheffield Island hotels

The Watershed - Formerly Hotel Zero Degrees
5/5 Excellent
"My family and I always choose the Watershed whenever we visit Connecticut. It never disappoints, Sienna the restaurant is also a huge plus"
A verified traveler stayed at The Watershed - Formerly Hotel Zero Degrees
Posted 23 hours ago
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