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Sheffield Island Vacation Rentals

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Oct 10 - Oct 12
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Jan 16 - Jan 18

Vacation Rentals in Sheffield Island

Stamford Suites
Lobby

Stamford Suites

4.0 star property
5.6 out of 10, (59)
"Great staff !!! "
The price is ￥19,737
￥22,697 total
includes taxes & fees
Oct 5 - Oct 6
Stamford Suites
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels

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!
Outdoor dining

Beechmont - Perfect for Family Retreat!

5.0 star property
The price is ￥78,075
￥142,109 total
includes taxes & fees
Sep 29 - Sep 30
Beechmont - Perfect for Family Retreat!
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

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

9.4 out of 10, Exceptional, (13)
"Perfect place to rest. Excellent service! "
The price is ￥11,301
￥29,739 total
includes taxes & fees
Oct 6 - Oct 7
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Guesthouse at Norwalk Inn
Standard Room, 1 King Bed, Main Building | Property entrance

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 ￥37,196
￥42,776 total
includes taxes & fees
Oct 7 - Oct 8
Guesthouse at Norwalk Inn
Business or Weekend escape
Pool

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 ￥12,707
￥21,901 total
includes taxes & fees
Sep 29 - Sep 30
Business or Weekend escape
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Terrace/patio

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
Global Luxury Suites White Plains
Reception

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!
Smart TV, stereo

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 ￥107,633
￥204,278 total
includes taxes & fees
Sep 29 - Sep 30
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
price will make you book twice , luxury living
Fridge, microwave, oven, stovetop

price will make you book twice , luxury living

10.0 out of 10, Exceptional, (1)
"We had a great stay! Room was very open and clean and our host was friendly and welcoming! "
The price is ￥18,836
￥24,651 total
includes taxes & fees
Sep 29 - Sep 30
price will make you book twice , luxury living
Luxury Apartments by Hyatus at The Asher
Lounge

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
Charming 3-bedroom modern family retreat!
Property grounds

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 ￥61,291
￥88,130 total
includes taxes & fees
Oct 12 - Oct 13
Charming 3-bedroom modern family retreat!
Elegant Hideaway • Free Parking
1 bedroom, iron/ironing board, free WiFi, bed sheets

Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking
Luxury Designer 2 bedroom+office/3bed vacation home.
Property grounds

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

9.4 out of 10, Exceptional, (20)
"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. "
The price is ￥25,159
￥67,353 total
includes taxes & fees
Sep 29 - Sep 30
Luxury Designer 2 bedroom+office/3bed vacation home.
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Property grounds

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 ￥79,917
￥141,517 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Chic Private 1BR Suite/Walk to Shops
Property grounds

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 ￥33,635
￥42,884 total
includes taxes & fees
Sep 29 - Sep 30
Chic Private 1BR Suite/Walk to Shops
Centric property close to all the great things in the city
Fridge, oven, stovetop, coffee/tea maker

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 ￥23,545
￥45,054 total
includes taxes & fees
Sep 29 - Sep 30
Centric property close to all the great things in the city
Charming 2-bedroom house with WiFi, AC in Fairfield
Interior

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 ￥8,745
￥34,574 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2-bedroom house with WiFi, AC in Fairfield
Modern 2 Bed in BlackRock
Exterior

Modern 2 Bed in BlackRock

2.0 star property
6.8 out of 10, (3)
"Cozy get away"
The price is ￥23,993
￥54,912 total
includes taxes & fees
Oct 20 - Oct 21
Modern 2 Bed in BlackRock
Flex Comfort Apts of Greenwich #1
Exterior

Flex Comfort Apts of Greenwich #1

8.8 out of 10, Excellent, (20)
"This was my 3rd time staying at this location. It is in a safe and easy location, close to the downtown area and train. Quiet and very clean with all of the amenities needed to have a comfortable stay. The host was very responsive in getting back to me quickly in one inquiry made. I would be very glad to stay there again."
Flex Comfort Apts of Greenwich #1
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

East Norwich Inn

East Norwich Inn

10/10 Excellent
"Clean, quiet, with a friendly staff that is always ready to assist. House keeping is great. Wish there was a breakfast and wish the gym was not so isolated in the basement. "
Anne 2-night trip
Posted 1 day ago
East Norwich Inn

Find out more about Sheffield Island

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
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Look no further and take a look at our great range of rental properties in Sheffield Island!

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Frequently asked questions

Are there vacation rentals in Sheffield Island?

Yes, we have vacation rentals close to top sights in Sheffield Island, or you can go with a more remote option if you'd like a relaxing place to stay. Sheffield Island is known for its monuments.

What's the top vacation rental that Sheffield Island has to offer?

Beechmont - Perfect for Family Retreat!: This vacation 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 vacation with a private yard 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 larger area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a vacation rental in Sheffield Island like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sheffield Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.