Photo by Richard Miska

Sheffield Island holiday rentals

We found 307 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Sheffield Island to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Sheffield Island

Showing deals for:3 Oct - 10 Oct
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Take in the waterfront beauty of Sheffield Island

Enjoy the monuments and other features of Sheffield Island. One of the city's many top draws is its island views. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Sheffield Island

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sheffield Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (3.4 mi / 5.4 km)
  • Chelsea Piers (5.1 mi / 8.2 km)
  • Del Vino Vineyards (10.7 mi / 17.2 km)
  • Bayville Adventure Park (13.1 mi / 21.1 km)
  • Cold Spring Harbor Laboratory (13.5 mi / 21.7 km)
  • Rye Playland (14.6 mi / 23.5 km)

Exploring the natural features in Sheffield Island

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Sheffield Island. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Calf Pasture Beach (2.8 mi / 4.5 km)
  • Cove Island Park (4.4 mi / 7 km)
  • Compo Beach (4.9 mi / 7.9 km)
  • Cummings Park Beach (5.4 mi / 8.6 km)
  • Cummings Park (5.4 mi / 8.7 km)
  • Old Mill Beach (5.5 mi / 8.8 km)

Travelling to and around Sheffield Island

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 15 mi (24.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 16.7 mi (26.9 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Sheffield Island?
Property type, length of stay and time of year are some things that can determine the price of a holiday home. Simply click on your travel dates to find your perfect escape. From cosy cabins to sprawling villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Sheffield Island?
The average price for a holiday home by the beach in Sheffield Island depends on when you're going and the size and style of property you're looking for. You can find prices quickly and easily on Stayz by entering your dates of travel. Then use the handy filters to select the number of bedrooms and amenities essential to you, like air conditioning, WiFi and a hot tub.
How old do you have to be to rent a holiday home in Sheffield Island?
You'll need to check with the Sheffield Island holiday property you'd like on Stayz as the minimum age differs. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Sheffield Island for?
It really depends on the Sheffield Island property. To browse available options offering extended stays, just enter your travel dates and number of guests into the Stayz search page. Enjoy having the place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a backyard where your little ones can play. Be on the lookout for any long-term stays that offer weekly or monthly discounts.

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