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Sheffield Island Vacation Rentals

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Check prices for these dates

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

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
The price is SAR 661
SAR 990 total
includes taxes & fees
16 Dec - 17 Dec
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
The price is SAR 552
SAR 634 total
includes taxes & fees
18 Nov - 19 Nov
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
The price is SAR 1,171
SAR 1,346 total
includes taxes & fees
1 Dec - 2 Dec
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
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.
The price is SAR 540
SAR 1,128 total
includes taxes & fees
23 Nov - 24 Nov
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.
The price is SAR 563
SAR 966 total
includes taxes & fees
22 Nov - 23 Nov
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.
The price is SAR 844
SAR 1,663 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is SAR 540
SAR 1,093 total
includes taxes & fees
23 Nov - 24 Nov
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.
The price is SAR 456
SAR 640 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is SAR 842
SAR 1,669 total
includes taxes & fees
17 Nov - 18 Nov
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.
The price is SAR 540
SAR 1,492 total
includes taxes & fees
18 Nov - 19 Nov
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
The price is SAR 706
SAR 1,030 total
includes taxes & fees
1 Dec - 2 Dec
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
The price is SAR 837
SAR 1,519 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is SAR 525
SAR 833 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is SAR 856
SAR 2,202 total
includes taxes & fees
16 Nov - 17 Nov
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
The price is SAR 338
SAR 541 total
includes taxes & fees
16 Nov - 17 Nov
Business or Weekend escape
A modern living room with a blue sofa, a dining table with chairs, and a large window with blinds.

17. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is SAR 657
SAR 966 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is SAR 1,020
SAR 2,449 total
includes taxes & fees
18 Nov - 19 Nov
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.
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.
The price is SAR 602
SAR 1,322 total
includes taxes & fees
19 Nov - 20 Nov
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

A modern lounge area with a stone fireplace, leather seating, and large windows offering a view of the city.
Residence Inn by Marriott Norwalk

Residence Inn by Marriott Norwalk

Residence Inn by Marriott Norwalk
South Norwalk

10/10 Excellent

Well maintained and it was easy to get in and out of the hotel
United States
Jeff
Reviewed April 7, 2024
Residence Inn by Marriott Norwalk

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.