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Sheffield Island Holiday Rentals

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Holiday Rentals in Sheffield Island

Stamford Suites

4.0 star property
5.6 out of 10, (55)
"Excellent sleep"
The price is AU$230
includes taxes & fees
29 Sept - 30 Sept
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (71)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Beechmont - Perfect for Family Retreat!

5.0 star property
The price is AU$1,440
includes taxes & fees
25 Sept - 26 Sept
Beechmont - Perfect for Family Retreat!

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

9.4 out of 10, Exceptional, (12)
"Perfect place to rest. Excellent service! "
The price is AU$309
includes taxes & fees
29 Sept - 30 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is AU$452
includes taxes & fees
13 Oct - 14 Oct
Guesthouse at Norwalk Inn

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

8.8 out of 10, Excellent, (8)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

Business or Weekend escape

9.2 out of 10, Wonderful, (46)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is AU$225
includes taxes & fees
28 Sept - 29 Sept
Business or Weekend escape

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."
Global Luxury Suites White Plains

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (2)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is AU$2,113
includes taxes & fees
29 Sept - 30 Sept
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Charming 3-bedroom modern family retreat!

9.0 out of 10, Wonderful, (4)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is AU$830
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom modern family retreat!

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!"
Luxury Apartments by Hyatus at The Asher

Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (10)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is AU$1,449
includes taxes & fees
30 Sept - 1 Oct
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

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

9.4 out of 10, Exceptional, (20)
"The furniture was comfortable, neat, and clean. Only one bathroom and on second floor, otherwise nice place, and owner responded fast. "
The price is AU$585
includes taxes & fees
25 Sept - 26 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.

Chic Private 1BR Suite/Walk to Shops

9.0 out of 10, Wonderful, (2)
"Vanessa is very responsive and laid back. She made the booking and check-in process seamless and the location of her property is stellar. The neighborhood is great to walk dogs and safe. "
The price is AU$440
includes taxes & fees
30 Sept - 1 Oct
Chic Private 1BR Suite/Walk to Shops

Centric property close to all the great things in the city

7.6 out of 10, Good, (12)
"This rental was great accommodation"
The price is AU$458
includes taxes & fees
28 Sept - 29 Sept
Centric property close to all the great things in the city

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

2.0 out of 10, (1)
"While we received multiple confirmations of our reservation, including the morning we were to check in, the property manager never sent us check in instructions, even after we emailed asking for them. Then, after spending over an hour with multiple calls to VRBO customer service, who also couldn’t get ahold of the property manager, we arrived at the location. There was a 4ft high, 10ft wide heap of garbage in the front yard and looking in through the windows it was apparent the house was under...
The price is AU$1,677
includes taxes & fees
1 Oct - 2 Oct
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (5)
Soothing Carriage House with Hot Tub in charming Stratford

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (8)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is AU$354
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house with WiFi, AC in Fairfield

price will make you book twice , luxury living

The price is AU$277
includes taxes & fees
28 Sept - 29 Sept
price will make you book twice , luxury living
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

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$225 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?

Beechmont - Perfect for Family Retreat!: This holiday home rental outside 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.