Sheffield Island Holiday Rentals

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Our top choices for Sheffield Island holiday rentals

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (80 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
4.0 star property
The price is AU$1,090
includes taxes & fees
23 Mar - 24 Mar
Luxury NYC Home Game Room Free Parking
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$413
includes taxes & fees
20 Mar - 21 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
5.0 star property
The price is AU$1,949
includes taxes & fees
16 Mar - 17 Mar
Beechmont - Perfect for Family Retreat!
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$498
includes taxes & fees
13 Apr - 14 Apr
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
2.0 star property
The price is AU$774
includes taxes & fees
14 Mar - 15 Mar
Luxury 3BR Home Game Room Free Parking

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$583
includes taxes & fees
14 Mar - 15 Mar
Guesthouse at Norwalk Inn
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is AU$541
includes taxes & fees
14 Mar - 15 Mar
Luxe Provincial Style Studio w/ Patio & Parking

Holiday Home in Brooklawn - St. Vincent

Centric property close to all the great things in the city
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AU$421
includes taxes & fees
14 Mar - 15 Mar
Centric property close to all the great things in the city
10.0 out of 10, Exceptional, (28 reviews)
"Everything was great. Even had TP sent via Amazon before arrival and told us to open and take inside. Would definitely stay here again. "
United States
Travis W.
The price is AU$678
includes taxes & fees
19 Mar - 20 Mar
Cozy Cottage with Fire Pit, near Beach
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is AU$541
includes taxes & fees
14 Mar - 15 Mar
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is AU$532
includes taxes & fees
14 Mar - 15 Mar
Elegant Hideaway with Free Parking

Holiday Home in White Plains

Luxury NY Home with Free Parking
4.0 star property
8.0 out of 10, Very good, (1 review)
"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$722
includes taxes & fees
15 Mar - 16 Mar
Luxury NY Home with Free Parking

Holiday Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
New Beach Home near Stamford Downtown/Shippan

Apartment in Huntington Station

THE OASIS @ LONG ISLAND
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is AU$672
includes taxes & fees
15 Mar - 16 Mar
THE OASIS @ LONG ISLAND

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is AU$561
includes taxes & fees
16 Mar - 17 Mar
Seabreeze at the beach west beach Stamford ct.

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (75 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is AU$675
includes taxes & fees
23 Mar - 24 Mar
Captain's Cottage - Cold Spring Harbor Water Views

Holiday Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$210
includes taxes & fees
26 Mar - 27 Mar
Business or Weekend escape
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is AU$1,037
includes taxes & fees
17 Mar - 18 Mar
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is AU$604
includes taxes & fees
20 Mar - 21 Mar
Luxury Designer 2 bedroom+office/3bed vacation home.
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$210 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, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Sheffield Island is equipped with a garden, air conditioning and WiFi 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.