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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Sheffield Island vacation rentals

Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (98 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is P12,083
P17,655 total
includes taxes & fees
Aug 4 - Aug 5
DUNE Fairfield Beach
Dining

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, (1 review)
"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 P21,568
P35,052 total
includes taxes & fees
Jul 13 - Jul 14
Luxury NYC Home with Free Parking for 12
Living area

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 P21,568
P33,850 total
includes taxes & fees
Jul 12 - Jul 13
Luxury NYC Home Game Room Free Parking
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is P37,625
P64,837 total
includes taxes & fees
Jul 12 - Jul 13
Beechmont - Perfect for Family Retreat!
Interior

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 P27,361
P41,868 total
includes taxes & fees
Aug 2 - Aug 3
4 Mi to Beach & Dtwn! Charming Fairfield Home
Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is P12,263
P23,208 total
includes taxes & fees
Aug 4 - Aug 5
Elegant Hideaway with Free Parking
Property entrance

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 P22,090
P25,404 total
includes taxes & fees
Jul 19 - Jul 20
Guesthouse at Norwalk Inn
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (135 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is P9,810
P11,282 total
includes taxes & fees
Jul 26 - Jul 27
Stamford Suites
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is P40,055
P53,793 total
includes taxes & fees
Jul 13 - Jul 14
Prime Luxe 3-BR NYC - Free Parking
In-room dining

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 P61,623
P77,814 total
includes taxes & fees
Jul 13 - Jul 14
3BR Prime Luxury NY - Free Parking
4 bedrooms, Internet

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is P63,099
P88,721 total
includes taxes & fees
Jul 24 - Jul 25
Stareway to Heaven in Fairfield
Interior

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 P15,629
P28,794 total
includes taxes & fees
Jul 15 - Jul 16
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

The Stamford Hotel

The Stamford Hotel

8/10 Good
"Good location, clean rooms, very nice pub meal, friendly and helpful staff."
christopher 1-night trip
Posted 3 hours ago
The Stamford 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:

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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 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 SoNo Switch Tower Museum.

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.