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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Sheffield Island vacation rentals

Standard Room, 1 King Bed, Main Building | Property entrance

1. 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
The price is ￥33,473
￥38,494 total
includes taxes & fees
Sep 15 - Sep 16
Guesthouse at Norwalk Inn
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,394
￥40,921 total
includes taxes & fees
Sep 28 - Sep 29
DUNE Fairfield Beach
Exterior

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (173 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥24,579
￥28,265 total
includes taxes & fees
Sep 20 - Sep 21
Stamford Suites
1 bedroom, desk, WiFi, bed sheets

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
The price is ￥20,225
￥37,926 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Studio with Pool Table
Dining

5. Romantic Hide Out

Romantic Hide Out
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 ￥16,559
￥37,135 total
includes taxes & fees
Sep 17 - Sep 18
Romantic Hide Out
Offices

6. 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 ￥24,702
￥51,566 total
includes taxes & fees
Sep 28 - Sep 29
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds

7. 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
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥29,529
￥57,723 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

8. 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, (12 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is ￥16,520
￥29,188 total
includes taxes & fees
Oct 5 - Oct 6
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Smart TV

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.
The price is ￥22,078
￥64,026 total
includes taxes & fees
Sep 17 - Sep 18
Modern Luxe 1BR Apt in Downtown Stamford
Property grounds

10. 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, (16 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥34,911
￥84,305 total
includes taxes & fees
Sep 29 - Sep 30
Seabreeze at the beach west beach Stamford ct.
2 bedrooms, iron/ironing board, WiFi, bed sheets

11. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥35,877
￥65,483 total
includes taxes & fees
Sep 13 - Sep 14
Gilded Age Luxury Surrounded by Nature
Smart TV, fireplace, books, stereo

12. 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 ￥46,609
￥108,395 total
includes taxes & fees
Sep 16 - Sep 17
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
TV

13. 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 ￥46,317
￥90,781 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Stamford Home | Family, Work, Parking
Property grounds

14. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very Good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is ￥26,123
￥34,835 total
includes taxes & fees
Sep 12 - Sep 13
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Private kitchen

15. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥30,724
￥55,712 total
includes taxes & fees
Sep 27 - Sep 28
Modern Luxury 1BR Stamford Getaway
Coffee/tea maker, fridge, microwave, oven

16. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 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 ￥22,885
￥54,030 total
includes taxes & fees
Sep 21 - Sep 22
Modern 2 Bed in BlackRock
Coffee/tea maker, fridge, microwave, oven

17. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is ￥56,507
￥121,550 total
includes taxes & fees
Sep 24 - Sep 25
Spacious Retreat with Game Room and Fire Pit
Interior

18. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
The price is ￥21,158
￥60,515 total
includes taxes & fees
Sep 17 - Sep 18
Luxury Designer 2 bedroom+office/3bed vacation home.
Interior

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is ￥59,028
￥101,804 total
includes taxes & fees
Sep 23 - Sep 24
Nama-stay, sweet pink Saugatuck Shores beach cottage
Smart TV

20. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,148
￥39,500 total
includes taxes & fees
Sep 17 - Sep 18
Centric property close to all the great things in the city
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

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

8/10 Good
"Location is ok"
james 2-night trip
Posted 12 hours ago
EVEN Hotel Norwalk by IHG

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
  • Use the map to find apartments and other holiday homes in the Sheffield Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheffield Island while they last

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?

Business or Weekend escape: This vacation home rental outside of Sheffield Island offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.