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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sheffield Island vacation rentals

A beach with a wooden fence and rocks, leading to the water.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Nov 22 - Nov 23
Total with taxes and fees
DUNE Fairfield Beach
A modern hotel room with a large window, a sofa, a coffee table, and a decorative statue.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (210 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
$149 nightly
The price is $171
Nov 22 - Nov 23
Total with taxes and fees
Stamford Suites
A large, two-story building with a symmetrical facade, multiple windows, and a covered porch area.

3. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$298 nightly
The price is $343
Dec 1 - Dec 2
Total with taxes and fees
Guesthouse at Norwalk Inn
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

4. 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
$223 nightly
The price is $243
Nov 16 - Nov 17
Total with taxes and fees
Spacious Studio with Pool Table
A hallway with light wooden flooring, white walls, and a door leading to a room with a view.

5. 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.
$263 nightly
The price is $300
Nov 20 - Nov 21
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Living area

6. 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.
$226 nightly
The price is $258
Nov 22 - Nov 23
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A white picket fence with a gate, surrounded by lush greenery and white flowers.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
$389 nightly
The price is $443
Nov 16 - Nov 17
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
A house with a covered porch, a wooden fence, and a stone wall.

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.
$256 nightly
The price is $291
Nov 23 - Nov 24
Total with taxes and fees
Romantic hideout. 1Br. Lower Level
A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (35 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
$149 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
A gated outdoor area with a wooden fence, a metal gate, and a small table with a lamp.

10. 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, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
$390 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

11. 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.
$349 nightly
The price is $398
Nov 18 - Nov 19
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A spacious living area with a sofa, ottoman, and a blue chair. There is a kitchen area with a sink and cabinets, and a balcony with a view of buildings.

12. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
$241 nightly
The price is $274
Dec 1 - Dec 2
Total with taxes and fees
Stylish Home With Free ParkingZA
An outdoor seating area with a sofa, chairs, and a round table, surrounded by potted plants and candles.

13. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$357 nightly
The price is $408
Nov 18 - Nov 19
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

14. 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
9.4 out of 10, Exceptional, (19 reviews)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
$195 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

15. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
$515 nightly
The price is $587
Nov 16 - Nov 17
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
A swimming pool at night with blue lighting.

16. 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
$127 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
Business or Weekend escape
A spacious living area with a sofa, ottoman, and a blue chair. There is a kitchen area with a sink and cabinets, and a balcony with a view of buildings.

17. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
$214 nightly
The price is $244
Nov 16 - Nov 17
Total with taxes and fees
Stylish Home and Cozy200
A wooden deck with a table and chairs, surrounded by a railing and trees.

18. 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, (16 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.
$562 nightly
The price is $640
Nov 17 - Nov 18
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Exterior

19. Spacious 3BR | Family + Work | Ample Parking

Spacious 3BR | Family + Work | Ample Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"Great location - very spacious and strong AC! host was very communicative and easy to deal with."
United States
Cari B.
$423 nightly
The price is $482
Nov 16 - Nov 17
Total with taxes and fees
Spacious 3BR | Family + Work | Ample Parking
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

20. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
$298 nightly
The price is $339
Nov 19 - Nov 20
Total with taxes and fees
Modern 2 Bed in BlackRock
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Beautiful and close to great restaurants and shopping, friendly style comfortable room"
Tawni 1-night trip
Posted 1 hour ago
Norwalk Inn & Conference Center

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 $144 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.

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