A stone lighthouse with a white tower and black lantern room, surrounded by greenery and a clear blue sky.

Sheffield Island Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Sheffield Island vacation rentals

Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (145 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is ￥22,791
￥26,210 total
includes taxes & fees
Jul 30 - Jul 31
Stamford Suites
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (103 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is ￥31,341
￥46,035 total
includes taxes & fees
Aug 25 - Aug 26
DUNE Fairfield Beach
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥23,577
￥51,509 total
includes taxes & fees
Aug 1 - Aug 2
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is ￥29,489
￥38,008 total
includes taxes & fees
Aug 4 - Aug 5
2-bedroom apartmet No cleaning Fee
Standard Room, 1 King Bed, Main Building | 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 ￥58,779
￥67,596 total
includes taxes & fees
Jul 29 - Jul 30
Guesthouse at Norwalk Inn
1 bedroom, desk, iron/ironing board, WiFi (free)

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
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is ￥22,922
￥37,658 total
includes taxes & fees
Aug 2 - Aug 3
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
TV

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.4 out of 10, Very Good, (7 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥29,078
￥70,443 total
includes taxes & fees
Jul 30 - Jul 31
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Dining

Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is ￥17,841
￥39,686 total
includes taxes & fees
Aug 4 - Aug 5
Romantic Hide Out
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥23,592
￥67,924 total
includes taxes & fees
Jul 29 - Jul 30
Modern Luxe 1BR Apt in Downtown Stamford
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (17 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥34,482
￥65,032 total
includes taxes & fees
Aug 26 - Aug 27
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥27,179
￥48,939 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Studio with Pool Table
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 ￥27,703
￥36,942 total
includes taxes & fees
Aug 1 - Aug 2
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (58 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is ￥13,917
￥23,986 total
includes taxes & fees
Aug 5 - Aug 6
Business or Weekend escape
Coffee/tea maker, fridge, microwave, oven

Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is ￥33,094
￥48,625 total
includes taxes & fees
Jul 29 - Jul 30
Stylish Home With Free ParkingZA
Exterior

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is ￥19,905
￥29,294 total
includes taxes & fees
Jul 29 - Jul 30
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Private kitchen

Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥32,582
￥58,427 total
includes taxes & fees
Aug 8 - Aug 9
Modern Luxury 1BR Stamford Getaway
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is ￥22,104
￥48,219 total
includes taxes & fees
Jul 29 - Jul 30
Zen, Spacious & Comfy 2 bed, Lux beds
Coffee/tea maker, fridge, microwave, oven

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is ￥66,638
￥141,061 total
includes taxes & fees
Jul 29 - Jul 30
Stylish Beach Home near Stamford Downtown/Beach
Living area

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is ￥23,149
￥40,861 total
includes taxes & fees
Jul 29 - Jul 30
Welcoming 1 bedroom apartment in beautiful harbor village.
Smart TV, offices

Elegant Home

Elegant Home
Downtown Stamford
The price is ￥33,094
￥48,625 total
includes taxes & fees
Jul 29 - Jul 30
Elegant 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

Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

10/10 Excellent
"Everything was amazing will be back"
Tamseel 2-night trip
Posted 6 hours ago
Radisson Hotel Hauppauge-Long 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!

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation 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 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.