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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Sheffield Island vacation rentals

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

1. 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 ￥49,652
￥57,099 total
includes taxes & fees
Oct 31 - Nov 1
Guesthouse at Norwalk Inn
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (200 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥23,284
￥26,776 total
includes taxes & fees
Nov 8 - Nov 9
Stamford Suites
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,944
￥41,742 total
includes taxes & fees
Nov 17 - Nov 18
DUNE Fairfield Beach
An outdoor seating area with a round table, a chair, and a hanging light fixture.

4. 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)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is ￥35,317
￥73,326 total
includes taxes & fees
Nov 2 - Nov 3
Gem by the water+ firepit and all fenced backyard
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

5. 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)
"Great fenced in yard for our pup"
United States
Deb S.
The price is ￥35,435
￥72,445 total
includes taxes & fees
Nov 11 - Nov 12
Nama-stay, sweet pink Saugatuck Shores beach cottage
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

6. 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.
The price is ￥46,775
￥114,231 total
includes taxes & fees
Nov 1 - Nov 2
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

7. 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.
The price is ￥40,254
￥101,790 total
includes taxes & fees
Oct 28 - Oct 29
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

8. 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 ￥37,798
￥98,668 total
includes taxes & fees
Nov 15 - Nov 16
Seabreeze at the beach west beach Stamford ct.
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.

9. 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, (32 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.
The price is ￥65,043
￥136,885 total
includes taxes & fees
Nov 1 - Nov 2
5BR Beach House, Water Views, Steps to Beach, Backyard
A spacious room with wooden beams, a hanging chair, and clear chairs.

10. Designer Treehouse with Spa Bath

Designer Treehouse with Spa Bath
Wilton
9.4 out of 10, Exceptional, (3 reviews)
"We came to stay near our son at Sacred Heart. The neighborhood is cute, the house is a perfect size and the location was close to everything we needed."
United States
Sarah M.
The price is ￥37,640
￥92,580 total
includes taxes & fees
Oct 28 - Oct 29
Designer Treehouse with Spa Bath
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

11. 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
Living area

12. 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 ￥23,624
￥42,287 total
includes taxes & fees
Oct 28 - Oct 29
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

13. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is ￥47,090
￥60,138 total
includes taxes & fees
Oct 28 - Oct 29
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

14. 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 ￥22,679
￥65,296 total
includes taxes & fees
Nov 1 - Nov 2
Modern Luxe 1BR Apt in Downtown Stamford
A living room with a sofa, armchair, ottoman, and coffee table.

15. 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.
The price is ￥37,483
￥80,116 total
includes taxes & fees
Nov 10 - Nov 11
Spacious Stamford Home | Family, Work, Parking
A modern living room with a white sofa, a glass coffee table, and a piano.

16. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is ￥54,177
￥103,960 total
includes taxes & fees
Nov 2 - Nov 3
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A modern living room with a sofa, a coffee table, and a bar stool.

17. 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 ￥22,679
￥49,074 total
includes taxes & fees
Oct 28 - Oct 29
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern kitchen with white cabinets, a marble island, and black bar stools.

18. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is ￥54,807
￥119,313 total
includes taxes & fees
Nov 18 - Nov 19
Spacious Retreat with Game Room and Fire Pit
Open concept kitchen

19. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (26 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
The price is ￥64,886
￥147,816 total
includes taxes & fees
Oct 29 - Oct 30
5BR Beach House, Game Room + Huge Backyard
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

20. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥26,222
￥53,622 total
includes taxes & fees
Oct 30 - Oct 31
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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

The Stamford Hotel

The Stamford Hotel

10/10 Excellent
"Beautiful hotel. Free coffee bar in the lobby. Staff was so helpful."
Jessica 2-night trip
Posted less than an hour ago
The Stamford Hotel

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?

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.