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

Sheffield Island Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Sheffield Island vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (193 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$164 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
Stamford Suites
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Oct 29 - Oct 30
Total with taxes and fees
DUNE Fairfield Beach
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. 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
$330 nightly
The price is $380
Oct 18 - Oct 19
Total with taxes and fees
Guesthouse at Norwalk Inn
Interior

4. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
$237 nightly
The price is $269
Oct 17 - Oct 18
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A bedroom with a bed, a nightstand, a dresser, a window with blinds, and a radiator.

5. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
$412 nightly
The price is $521
Oct 19 - Oct 20
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

6. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
10.0 out of 10, Exceptional, (1 review)
"This was a great deal on the busy weekend we stayed. The space was even better than described."
United States
Derek H.
$261 nightly
The price is $297
Oct 16 - Oct 17
Total with taxes and fees
Modern Apartment with Private Entrance
A modern living room with a sofa, a coffee table, and a bar stool.

7. 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.
$275 nightly
The price is $312
Oct 18 - Oct 19
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern living room with a flat-screen TV, a fireplace, a round marble table with a bowl of grapes, and a floor lamp.

8. Romantic hideout. 1Br. Lower Level

Romantic hideout. 1Br. Lower Level
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.
$269 nightly
The price is $339
Oct 20 - Oct 21
Total with taxes and fees
Romantic hideout. 1Br. Lower Level
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

9. 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.
$368 nightly
The price is $417
Oct 16 - Oct 17
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A modern kitchen with white cabinetry, a stainless steel refrigerator, a dishwasher, and a microwave.

10. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$498 nightly
The price is $636
Oct 18 - Oct 19
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

11. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern kitchen with a central island, pendant lights, and built-in shelves.

12. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
$272 nightly
The price is $308
Nov 2 - Nov 3
Total with taxes and fees
Stylish Home With Free ParkingZA
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

13. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
$478 nightly
The price is $542
Nov 2 - Nov 3
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
$327 nightly
The price is $371
Nov 15 - Nov 16
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

15. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (18 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
$485 nightly
The price is $549
Oct 18 - Oct 19
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

16. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
$591 nightly
The price is $670
Nov 9 - Nov 10
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern living room with a large window, a sofa, a coffee table, and a TV.

17. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (14 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
$171 nightly
The price is $194
Oct 20 - Oct 21
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A living room with a sofa set, a coffee table, and a television on a stand.

18. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$516 nightly
The price is $584
Oct 16 - Oct 17
Total with taxes and fees
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

19. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
$916 nightly
The price is $972
Oct 20 - Oct 21
Total with taxes and fees
5BR Beach House, Water Views, Steps to Beach, Backyard
A swimming pool at night with blue lighting.

20. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$135 nightly
The price is $152
Oct 18 - Oct 19
Total with taxes and fees
Business or Weekend escape
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

HYATT house White Plains

HYATT house White Plains

10/10 Excellent
"Good breakfast, clean rooms and excellent service"
Laura Rebeca 8-night trip
Posted 10 hours ago
HYATT house White Plains

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 $152 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?

5BR Beach House, Game Room + Huge Backyard: This vacation home rental outside of Sheffield Island is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden 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.