Photo by Richard Miska

Sheffield Island Holiday Rentals

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Check prices for these dates

Tonight
1 Nov - 2 Nov
Tomorrow
2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Holiday Rentals in Sheffield Island

Lobby
Stamford Suites
Stamford Suites
4.0 star property
6.0 out of 10, (67)
"Location very good."
United States
Sheila
The price is HK$938
HK$1,078 total
includes taxes & fees
2 Nov - 3 Nov
Stamford Suites
Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (75)
"Great stay"
Canada
Gilles
DUNE Fairfield Beach
Lounge
Luxury Apartments by Hyatus at The Asher
Luxury Apartments by Hyatus at The Asher
4.5 star property
10.0 out of 10, Exceptional, (18)
"This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!"
United States
Tasha
Luxury Apartments by Hyatus at The Asher
Reception
Global Luxury Suites White Plains
Global Luxury Suites White Plains
3.5 star property
6.8 out of 10, (32)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (19)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is HK$594
HK$1,554 total
includes taxes & fees
2 Nov - 3 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property entrance
Guesthouse at Norwalk Inn
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
United States
Brian
The price is HK$2,038
HK$2,344 total
includes taxes & fees
6 Nov - 7 Nov
Guesthouse at Norwalk Inn
Outdoor dining
Beechmont - Perfect for Family Retreat!
Beechmont - Perfect for Family Retreat!
5.0 star property
The price is HK$4,651
HK$8,069 total
includes taxes & fees
2 Nov - 3 Nov
Beechmont - Perfect for Family Retreat!
Pool
Business or Weekend escape
Business or Weekend escape
9.2 out of 10, Wonderful, (50)
"Loved all the different things on the walls, the only negative thing i have to say is that the driveway was very narrow and hard to park my truck in with others parked on the street."
United States
Jeffrey S.
The price is HK$622
HK$1,094 total
includes taxes & fees
2 Nov - 3 Nov
Business or Weekend escape
55-inch Smart TV with digital channels, TV, streaming services
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
9.6 out of 10, Exceptional, (4)
"Extremely clean and well prepared home stocked with items we may need. Plenty of space for all guests. Comfortable beds. Felt safe with the use of electronic keypad entry and security system. Very well maintained. Historic feel with modern amenities. Great location in regards to where we needed to be. Able to communicate with host who assisted in accommodations. Plenty of parking. Lovely place. "
United States
natalie c.
The price is HK$5,595
HK$10,742 total
includes taxes & fees
2 Nov - 3 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
1 bedroom, iron/ironing board, free WiFi, bed sheets
Elegant Hideaway • Free Parking
Elegant Hideaway • Free Parking
Elegant Hideaway • Free Parking
Property grounds
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
9.2 out of 10, Wonderful, (12)
"This is a quiet and beautiful spot on the water. The outside space is perfect to relax or get some sun. The inside space was relaxing and very comfortable. The host, Richard was wonderful and very responsive. "
United States
Lori G.
The price is HK$3,476
HK$5,551 total
includes taxes & fees
2 Nov - 3 Nov
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"Don’t be worried about the neighborhood. It might be different than what you’re used to but it’s safe and a ton of local places to eat are great! Hosts are great and the space was excellent!!"
United States
Jack R.
The price is HK$1,308
HK$3,462 total
includes taxes & fees
2 Nov - 3 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
Private kitchen
Luxury NY Home with Free Parking
Luxury NY Home with Free Parking
4.0 star property
The price is HK$2,350
HK$3,457 total
includes taxes & fees
2 Nov - 3 Nov
Luxury NY Home with Free Parking
Property grounds
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
7.4 out of 10, Good, (3)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$1,748
HK$2,330 total
includes taxes & fees
2 Nov - 3 Nov
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Interior
Luxury NY Home with Game Room & Free Parking
Luxury NY Home with Game Room & Free Parking
2.0 star property
Luxury NY Home with Game Room & Free Parking
Property grounds
Curated Private One Bedroom Suite Steps from Shops, Equestrian Country & NYC 🏙️
Curated Private One Bedroom Suite Steps from Shops, Equestrian Country & NYC 🏙️
9.4 out of 10, Exceptional, (3)
"Clean and quiet."
United States
Gerhard P.
The price is HK$1,748
HK$2,229 total
includes taxes & fees
2 Nov - 3 Nov
Curated Private One Bedroom Suite Steps from Shops, Equestrian Country & NYC 🏙️
1 bedroom, WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is HK$804
HK$1,798 total
includes taxes & fees
2 Nov - 3 Nov
Newly renovated Private bedroom near Stony Brook University
Interior
Beautiful historic home in Stony Brook!
Beautiful historic home in Stony Brook!
2.0 star property
8.2 out of 10, Very good, (20)
"Thank you Great Location Would book again"
United States
M M.
Beautiful historic home in Stony Brook!
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
The price is HK$660
HK$1,272 total
includes taxes & fees
2 Nov - 3 Nov
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Lounge
Luxury Apartments by Hyatus White Plains
Luxury Apartments by Hyatus White Plains
4.5 star property
Luxury Apartments by Hyatus White Plains
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"The staff was great. "
Thomas 1-night trip
Posted 2 days ago
Norwalk Inn & Conference Center

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 are some of the best holiday rentals that Sheffield Island has to offer?

Beechmont - Perfect for Family Retreat!: This holiday home rental outside of Sheffield Island is located near the airport, and has a private balcony, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with a private garden and a selection of games.

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.