Sheffield Island Holiday Rentals

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Sheffield Island holiday rentals

Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$666
HK$1,147 total
includes taxes & fees
21 Apr - 22 Apr
Business or Weekend escape
2 bedrooms, iron/ironing board, travel cot, WiFi

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is HK$829
HK$2,238 total
includes taxes & fees
13 Apr - 14 Apr
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Private kitchen

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is HK$705
HK$2,446 total
includes taxes & fees
15 Apr - 16 Apr
Modern 1BR Apt / Free Parking / Near NYC
Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is HK$2,076
HK$3,542 total
includes taxes & fees
12 Apr - 13 Apr
Luxury NYC Home Game Room Free Parking
Living area

Cozy 1BR / 2 Queen Beds / Free Parking / Private Stay

Cozy 1BR / 2 Queen Beds / Free Parking / Private Stay
White Plains
The price is HK$635
HK$2,356 total
includes taxes & fees
26 Apr - 27 Apr
Cozy 1BR / 2 Queen Beds / Free Parking / Private Stay
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (84 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is HK$1,219
HK$1,880 total
includes taxes & fees
29 Apr - 30 Apr
DUNE Fairfield Beach
Fridge, microwave, oven, stovetop

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is HK$829
HK$2,238 total
includes taxes & fees
16 Apr - 17 Apr
Renovated 2BR Retreat / Modern Comforts Included
Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$2,734
HK$4,294 total
includes taxes & fees
7 May - 8 May
Luxury 3BR Home Game Room Free Parking
Smart TV

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.0 out of 10, Good, (14 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is HK$1,234
HK$2,330 total
includes taxes & fees
11 Apr - 12 Apr
Centric property close to all the great things in the city
Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$1,167
HK$2,967 total
includes taxes & fees
21 Apr - 22 Apr
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is HK$2,391
HK$2,749 total
includes taxes & fees
11 Apr - 12 Apr
Guesthouse at Norwalk Inn
Interior

Stamford CT Guest Suite. Spacious, private home for visiting family & friends

Stamford CT Guest Suite. Spacious, private home for visiting family & friends
Stamford
The price is HK$1,057
HK$2,481 total
includes taxes & fees
21 Apr - 22 Apr
Stamford CT Guest Suite. Spacious, private home for visiting family & friends
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is HK$1,199
HK$2,530 total
includes taxes & fees
12 Apr - 13 Apr
Zen, Spacious & Comfy 2 bed, Lux beds
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$2,350
HK$3,785 total
includes taxes & fees
1 May - 2 May
Prime Luxe 3-BR NYC - Free Parking
1 bedroom, desk, iron/ironing board, free WiFi

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.6 out of 10, Exceptional, (8 reviews)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is HK$1,096
HK$1,786 total
includes taxes & fees
16 Apr - 17 Apr
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
In-room dining

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is HK$7,832
HK$9,890 total
includes taxes & fees
13 Apr - 14 Apr
3BR Prime Luxury NY - 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
Greenwich
7.6 out of 10, Good, (4 reviews)
"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$1,326
HK$1,768 total
includes taxes & fees
22 Apr - 23 Apr
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Interior

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
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 HK$1,159
HK$3,283 total
includes taxes & fees
21 Apr - 22 Apr
Luxury Designer 2 bedroom+office/3bed vacation home.
2 bedrooms, WiFi, bed sheets

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Smithtown
6.8 out of 10, (3 reviews)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
The price is HK$1,222
HK$1,799 total
includes taxes & fees
18 Apr - 19 Apr
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Fridge, microwave, oven, stovetop

Stylish Home With Free ParkingFA

Stylish Home With Free ParkingFA
Downtown Stamford
The price is HK$1,144
HK$1,766 total
includes taxes & fees
12 Apr - 13 Apr
Stylish Home With Free ParkingFA
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

SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

6/10 Okay
"Good afternoon "
hany 1-night trip
Posted less than an hour ago
SureStay Plus by Best Western Woodbury Inn

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:

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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?

Business or Weekend escape: This holiday home rental outside of Sheffield Island offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.