Sheffield Island Vacation Rentals

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Vacation Rentals in Sheffield Island

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich CT

$235 nightly

$266 total

Dec 21 - Dec 22

Total with taxes and fees

With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of E. Gaynor Brennan Golf Course and Yale New Haven Health Long Ridge Medical Center.

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport CT

$1,403 nightly

$1,587 total

Dec 16 - Dec 17

Total with taxes and fees

With a stay at this vacation home in Bridgeport (North End), you'll be within a 15-minute walk of Svihra Park and St. Vincent's Medical Center.

Charming Home in Seaside

Bridgeport CT

With a stay at this vacation home in Bridgeport (South End), you'll be steps from University of Bridgeport and Seaside Park.

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY

$453 nightly

$518 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

A stay at this vacation home places you in the heart of Cold Spring Harbor, within a 15-minute walk of Cold Spring Harbor State Park and Dolan DNA Learning Center.

Kitchen

Washer

Stareway to Heaven Su

Fairfield CT

With a stay at this vacation home in Fairfield (Fairfield Beach), you'll be steps from South Pine Creek Beach and 8 minutes by foot from Pine Creek Par 3 Golf Course.

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport CT

Located in Westport, this vacation home is within a 5-minute drive of Levitt Pavilion and Westport Country Playhouse.

Kitchen

Washer

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Fairfield CT

With a stay at this vacation home in Fairfield, you'll be by the sea, just a 4-minute walk from South Benson Marina and 11 minutes by foot from Fairfield Museum and History Center.

Spacious 4-bedroom house in charming Rye with AC

Rye NY

$2,499 nightly

$2,499 total

Dec 16 - Dec 17

Total with taxes and fees

Located in Rye, Spacious 4-bedroom house in charming Rye with AC is a 5-minute drive from Rye Playland and 6 minutes from Emelin Theatre.

Business or Weekend escape

Stratford CT

$130 nightly

$147 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport NY

When you a stay at this vacation home in Northport, you'll be on the beach, within a 5-minute walk of Cow Harbor Park and Northport Village Park.

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Syosset NY

With a stay at this vacation home, you'll be centrally located in Jericho, within a 10-minute drive of Roosevelt Field Mall and Broadway Mall.

Ultra-Modern Luxe Sleek & Stunning Stay

White Plains NY

With a stay at this vacation home in White Plains, you'll be within a 15-minute drive of NewYork-Presbyterian - Westchester Hospital and The Westchester Mall.

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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.