A stone lighthouse with a white tower and black lantern room, surrounded by greenery and a clear blue sky.

Sheffield Island Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sheffield Island holiday rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is RM596
RM685 total
includes taxes & fees
12 Oct - 13 Oct
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is RM1,465
RM1,685 total
includes taxes & fees
4 Oct - 5 Oct
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is RM724
RM1,081 total
includes taxes & fees
7 Oct - 8 Oct
DUNE Fairfield Beach
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

4. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is RM1,342
RM2,060 total
includes taxes & fees
9 Oct - 10 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

5. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is RM731
RM1,444 total
includes taxes & fees
5 Oct - 6 Oct
Elegant Hideaway with Free Parking
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

6. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is RM4,247
RM6,312 total
includes taxes & fees
6 Oct - 7 Oct
Beechmont - Perfect for Family Retreat!
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

7. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is RM2,020
RM2,918 total
includes taxes & fees
3 Oct - 4 Oct
Luxury NYC Home Game Room Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

8. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (2 reviews)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is RM1,652
RM2,571 total
includes taxes & fees
3 Oct - 4 Oct
Luxury NYC Home with Free Parking for 12
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

9. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is RM3,489
RM4,493 total
includes taxes & fees
3 Oct - 4 Oct
Prime Luxe 3-BR NYC - Free Parking
A breakfast buffet with pastries, fruits, and a coffee station.

10. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is RM3,672
RM4,698 total
includes taxes & fees
3 Oct - 4 Oct
3BR Prime Luxury NY - Free Parking
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

11. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is RM2,485
RM3,776 total
includes taxes & fees
4 Oct - 5 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
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

Marriott Melville Long Island

Marriott Melville Long Island

8/10 Good
"Nice hotel, needs some modernization. Staff was nice, valet was a jerk."
Barbara A 1-night trip
Posted 2 hours ago
Marriott Melville Long Island

Find out more about Sheffield Island

Search for holiday rentals in Sheffield Island on Expedia.co.uk! 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
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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.