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Sheffield Island Holiday Rentals

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Holiday Rentals in Sheffield Island

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (76)
"It was great"
United States
Natalie
The price is AU$211
includes taxes & fees
30 Nov - 1 Dec
Stamford Suites

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$420
includes taxes & fees
21 Dec - 22 Dec
Guesthouse at Norwalk Inn

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$384
includes taxes & fees
7 Dec - 8 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$218
includes taxes & fees
30 Nov - 1 Dec
Business or Weekend escape

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is AU$1,802
includes taxes & fees
1 Dec - 2 Dec
Beechmont - Perfect for Family Retreat!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End
9.6 out of 10, Exceptional, (4)
"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "
United States
Nancy H.
The price is AU$2,138
includes taxes & fees
30 Nov - 1 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Elegant Hideaway • Free Parking

White Plains
10.0 out of 10, Exceptional, (1)
"This location was tranquil and close to everything I expected for meals and entertainment. Easy to get to and felt warm and inviting. Fayeem was responsive and helpful towards my requests. I look forward to staying here again. Thank you!"
United States
Moses A.
Elegant Hideaway • Free Parking

Luxury NY Home with Free Parking

4.0 star property
White Plains
8.0 out of 10, Very good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is AU$717
includes taxes & fees
30 Nov - 1 Dec
Luxury NY Home with Free Parking

Luxury Designer 2 bedroom+office/3bed vacation home.

Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is AU$689
includes taxes & fees
29 Nov - 30 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Downtown Bridgeport
10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is AU$254
includes taxes & fees
30 Nov - 1 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (12)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is AU$277
includes taxes & fees
5 Dec - 6 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Syosset
10.0 out of 10, Exceptional, (10)
"The location and house were perfect for a family reunion. The host, Satbir, was very attentive and responded quickly to issues. Great guy"
United States
Michael K.
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Stamford Grand Apartment + Cozy Den

2.0 star property
Downtown Stamford
9.6 out of 10, Exceptional, (4)
"Very nice stay."
United States
Anonymous traveller
Stamford Grand Apartment + Cozy Den

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AU$739
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views

Luxury Apartments by Hyatus White Plains

4.5 star property
White Plains
Luxury Apartments by Hyatus White Plains

The Bella Vista St James! Waterfront house with a beach dock and so much more!

Saint James
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
The price is AU$3,314
includes taxes & fees
30 Nov - 1 Dec
The Bella Vista St James! Waterfront house with a beach dock and so much more!

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Stony Brook
6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
The price is AU$775
includes taxes & fees
30 Nov - 1 Dec
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
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

Find out more about Sheffield Island

Everything you need to know about Sheffield Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheffield Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sheffield Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheffield Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield Island holiday rentals we have selected for you start as low as AU$211 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sheffield Island rentals

At Expedia, we put the best Sheffield Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheffield Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheffield Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheffield Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday 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 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.