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Sheffield Island Vacation Rentals

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Oct 25 - Oct 26
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Oct 26 - Oct 27
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in Sheffield Island

Living area
The Mansion Hotel-style
The Mansion Hotel-style
4.5 star property
8.0 out of 10, Very Good, (2)
"Super clean, our host was a great, we felt valued and welcomed. 100% we will be staying at The Mansion Hotel. "
United States
Maslah
$141 nightly
The price is $163
Oct 27 - Oct 28
Total with taxes and fees
The Mansion Hotel-style
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (74)
"Loved this venue! "
United States
adriano
$232 nightly
The price is $267
Oct 26 - Oct 27
Total with taxes and fees
DUNE Fairfield Beach
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included
Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (1)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
$255 nightly
The price is $289
Oct 26 - Oct 27
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
Interior
Charming 2-bedroom house with WiFi, AC in Fairfield
Charming 2-bedroom house with WiFi, AC in Fairfield
8.4 out of 10, Very Good, (9)
"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."
United States
Tom F.
$243 nightly
The price is $275
Oct 26 - Oct 27
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in Fairfield
Pool
Business or Weekend escape
Business or Weekend escape
9.2 out of 10, Wonderful, (50)
"Great value!"
United States
Bruce H.
$125 nightly
The price is $141
Oct 26 - Oct 27
Total with taxes and fees
Business or Weekend escape
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (18)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$165 nightly
The price is $187
Oct 26 - Oct 27
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Fridge, microwave, oven, stovetop
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
8.0 out of 10, Very Good, (1)
"It was clean "
United States
Burton
$255 nightly
The price is $289
Oct 26 - Oct 27
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
$279 nightly
The price is $316
Oct 26 - Oct 27
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (10)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
$157 nightly
The price is $179
Oct 26 - Oct 27
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Interior
Sweet Studio w/ Lounge & Pool Table
Sweet Studio w/ Lounge & Pool Table
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
$223 nightly
The price is $253
Oct 26 - Oct 27
Total with taxes and fees
Sweet Studio w/ Lounge & Pool Table
1 bedroom, desk, iron/ironing board, free WiFi
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
9.0 out of 10, Wonderful, (6)
"The apartment was very clean with everything we needed for our stay. Outside noise was a little loud so I’d suggest a sound machine, but in case your forget the awesome host has supplied soft ear plugs for you. I would definitely visit again. "
United States
Chrystie
$203 nightly
The price is $230
Oct 26 - Oct 27
Total with taxes and fees
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Outdoor dining
Beechmont - Perfect for Family Retreat!
Beechmont - Perfect for Family Retreat!
5.0 star property
$981 nightly
The price is $1,128
Oct 27 - Oct 28
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"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. "
United States
Tessa P.
$337 nightly
The price is $382
Oct 27 - Oct 28
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
2 bedrooms, WiFi, bed sheets
Zen, Spacious & Comfy 2 bed, Lux beds
Zen, Spacious & Comfy 2 bed, Lux beds
$288 nightly
The price is $326
Oct 27 - Oct 28
Total with taxes and fees
Zen, Spacious & Comfy 2 bed, Lux beds
Exterior
The Bella Vista St James! Waterfront house with a beach dock and so much more!
The Bella Vista St James! Waterfront house with a beach dock and so much more!
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
$1,899 nightly
The price is $2,170
Oct 26 - Oct 27
Total with taxes and fees
The Bella Vista St James! Waterfront house with a beach dock and so much more!
Coffee/tea maker, spices
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
10.0 out of 10, Exceptional, (5)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
United States
Patrick
$348 nightly
The price is $398
Oct 26 - Oct 27
Total with taxes and fees
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
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
10.0 out of 10, Exceptional, (5)
"Lovely little home in Stamford."
United States
Pat A.
$295 nightly
The price is $333
Oct 27 - Oct 28
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Fridge, microwave, oven, stovetop
Marine Theme - 4 BR - Backyard - Fire pit
Marine Theme - 4 BR - Backyard - Fire pit
9.8 out of 10, Exceptional, (7)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
$406 nightly
The price is $460
Nov 4 - Nov 5
Total with taxes and fees
Marine Theme - 4 BR - Backyard - Fire pit
WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
$202 nightly
The price is $230
Oct 26 - Oct 27
Total with taxes and fees
Newly renovated Private bedroom near Stony Brook University
Fridge, microwave, oven, stovetop
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
10.0 out of 10, Exceptional, (1)
"Wonderful "
United States
Nolufefe Z.
$354 nightly
The price is $400
Oct 26 - Oct 27
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

10/10 Excellent
"Very accommodating, clean and modern"
Cliff 1-night trip
Posted 1 day ago
DoubleTree by Hilton Stamford

Find out more about Sheffield Island

Everything you need to know about Sheffield Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sheffield Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sheffield Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheffield Island rentals

At Expedia, we put the best Sheffield Island vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 of 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.