Photo by Richard Miska

Search Holiday Rentals in Sheffield Island

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Sheffield Island holiday rentals

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Stamford Suites

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (84)
"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 ฿3,426
฿3,940 total
includes taxes & fees
6 Jan - 7 Jan 2026
Stamford Suites
Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
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

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is ฿2,638
฿3,034 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Mansion Hotel-style
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
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 ฿8,659
฿9,958 total
includes taxes & fees
2 Jan - 3 Jan 2026
Guesthouse at Norwalk Inn
Luxury Villa, Garden View | Dining
Luxury NYC Home with Free Parking for 12

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is ฿13,966
฿21,110 total
includes taxes & fees
6 Jan - 7 Jan 2026
Luxury NYC Home with Free Parking for 12
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

Best Western Premier Plainview-Long Island Hotel

Best Western Premier Plainview-Long Island Hotel

10/10 Excellent
"My wife and i were in New York for an extended stay and this Best Western was absolutely amazing. It is on the service road but you don’t hear the highway noise once inside the hotel. The staff was so friendly and the place was spotless. This is a real find and so close to restaurants. It made out stay that much nicer."
Eric 8-night trip
Posted 1 day ago
Best Western Premier Plainview-Long Island Hotel

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 holiday rentals in Sheffield Island?

Yes, there are holiday rentals close to the most popular sights in Sheffield Island, or you can select a more secluded option if you're looking for a relaxing 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 wider area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a holiday rental in Sheffield Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheffield Island. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.