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Sheffield Island Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Sheffield Island vacation rentals

Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is NT$17,348
NT$24,541 total
includes taxes & fees
Dec 24 - Dec 25
Luxury NYC Home Game Room Free Parking
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is NT$2,681
NT$3,083 total
includes taxes & fees
Dec 27 - Dec 28
The Mansion Hotel-style
Lobby
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (82)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is NT$3,482
NT$4,004 total
includes taxes & fees
Dec 28 - Dec 29
Stamford Suites
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NT$8,800
NT$10,120 total
includes taxes & fees
Dec 28 - Dec 29
Guesthouse at Norwalk Inn
Private kitchen
Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is NT$3,470
NT$8,668 total
includes taxes & fees
Jan 6 - 2026/1/7
Elegant Hideaway with Free Parking
Apartment (1 Bedroom) | Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is NT$3,785
NT$8,679 total
includes taxes & fees
Dec 24 - Dec 25
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Free WiFi
Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is NT$6,277
NT$11,879 total
includes taxes & fees
Jan 6 - 2026/1/7
Luxury 3BR Home Game Room Free Parking
Luxury Apartment | Free WiFi
Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NT$6,277
NT$11,690 total
includes taxes & fees
Jan 6 - 2026/1/7
Prime Luxe 3-BR NYC - Free Parking
Luxury Villa, Garden View | Dining
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is NT$14,193
NT$21,454 total
includes taxes & fees
Jan 6 - 2026/1/7
Luxury NYC Home with Free Parking for 12
Front of property
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NT$26,691
NT$41,734 total
includes taxes & fees
Dec 30 - Dec 31
Beechmont - Perfect for Family Retreat!
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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Top Sheffield Island Hotel Reviews

Hilton Garden Inn Melville

Hilton Garden Inn Melville

10/10 Excellent
"Yes nice n clean"
Mohammed 1-night trip
Posted 2 days ago
Hilton Garden Inn Melville

Find out more about Sheffield Island

Search for holiday rentals in Sheffield Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield Island using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield Island
  • Use the map to find apartments and other holiday homes in the Sheffield Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheffield Island while they last

Look no further and take a look at our great range of rental properties in Sheffield Island!

Frequently asked questions

Are there vacation rentals in Sheffield Island?

Yes, we have vacation rentals close to top sights in Sheffield Island, or you can go with a more remote option if you'd like a relaxing place to stay. Sheffield Island is known for its monuments.

What’s there to see and do in Sheffield Island?

Explore the area and family-friendly sights such as Norwalk Maritime Aquarium, or get out into nature at a spot like Calf Pasture Beach. In the larger area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a vacation rental in Sheffield Island like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sheffield Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.