Photo by Richard Miska

Sheffield Island Vacation Rentals

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Check prices for these dates

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

Our top choices for Sheffield Island vacation rentals

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
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 ￥43,294
￥49,788 total
includes taxes & fees
Jan 3 - Jan 4
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 ￥70,403
￥106,416 total
includes taxes & fees
Jan 4 - Jan 5
Luxury NYC Home with Free Parking for 12
Apartment (1 Bedroom) | Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is ￥24,563
￥49,706 total
includes taxes & fees
Jan 4 - Jan 5
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Free WiFi
Luxury 3BR Home Game Room Free Parking

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is ￥31,134
￥58,920 total
includes taxes & fees
Jan 20 - Jan 21
Luxury 3BR Home Game Room Free Parking
Luxury Apartment | Free WiFi
Prime Luxe 3-BR NYC - Free Parking

Apartment in White Plains

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
The price is ￥31,134
￥57,986 total
includes taxes & fees
Jan 4 - Jan 5
Prime Luxe 3-BR NYC - Free Parking
Private kitchen
Elegant Hideaway with Free Parking

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is ￥15,674
￥41,282 total
includes taxes & fees
Jan 26 - Jan 27
Elegant Hideaway with Free Parking
Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Luxury NYC Home Game Room Free Parking

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is ￥86,048
￥121,729 total
includes taxes & fees
Jan 4 - Jan 5
Luxury NYC Home Game Room Free Parking
Front of property
Beechmont - Perfect for Family Retreat!

Vacation Home in North End

Beechmont - Perfect for Family Retreat!
5.0 star property
The price is ￥132,640
￥207,395 total
includes taxes & fees
Jan 5 - Jan 6
Beechmont - Perfect for Family Retreat!
Lobby
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 ￥18,774
￥21,590 total
includes taxes & fees
Jan 21 - Jan 22
Stamford Suites
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

Red Carpet Inn

Red Carpet Inn

10/10 Excellent
"It was decent for a nights rest an hour away from the city. Not bad "
Roxxanna 1-night trip
Posted 2 days ago
Red Carpet Inn

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 the top vacation rental that Sheffield Island has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental outside of Sheffield Island is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.