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Our top choices for Sheffield Island holiday rentals

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 £183
includes taxes & fees
15 Sept - 16 Sept
Guesthouse at Norwalk Inn

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (112 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is £196
includes taxes & fees
28 Sept - 29 Sept
DUNE Fairfield Beach

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (171 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is £131
includes taxes & fees
7 Sept - 8 Sept
Stamford Suites

4. 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 £238
includes taxes & fees
7 Sept - 8 Sept
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

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 £186
includes taxes & fees
11 Sept - 12 Sept
Romantic Hide Out

6. 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 £201
includes taxes & fees
15 Sept - 16 Sept
Spacious Studio with Pool Table

7. 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
9.8 out of 10, Exceptional, (17 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is £175
includes taxes & fees
7 Sept - 8 Sept
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

8. 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 £316
includes taxes & fees
9 Sept - 10 Sept
Modern Luxe 1BR Apt in Downtown Stamford

9. 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, (18 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is £288
includes taxes & fees
15 Sept - 16 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10. 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 £271
includes taxes & fees
7 Sept - 8 Sept
Modern Luxury 1BR Stamford Getaway

11. 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 £393
includes taxes & fees
29 Sept - 30 Sept
Seabreeze at the beach west beach Stamford ct.

12. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is £312
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature

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 £410
includes taxes & fees
9 Sept - 10 Sept
Spacious Stamford Home | Family, Work, Parking

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (27 reviews)
"The property was very easy to find, clean, and comfortable. The hosts were very communicative and accommodating. Highly recommend!"
United States
Karen D.
The price is £135
includes taxes & fees
8 Sept - 9 Sept
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

15. 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 £526
includes taxes & fees
7 Sept - 8 Sept
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

16. 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 £169
includes taxes & fees
12 Sept - 13 Sept
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

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 £537
includes taxes & fees
10 Sept - 11 Sept
Spacious Retreat with Game Room and Fire Pit

18. 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 £246
includes taxes & fees
14 Sept - 15 Sept
Modern 2 Bed in BlackRock

19. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is £224
includes taxes & fees
7 Sept - 8 Sept
Zen, Spacious & Comfy 2 bed, Lux beds

20. 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, (26 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is £301
includes taxes & fees
14 Sept - 15 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.
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

Find out more about Sheffield Island

Everything you need to know about Sheffield Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheffield Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield Island holiday rentals we have selected for you start as low as £116 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheffield Island rentals

At Expedia, we put the best Sheffield Island holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Sheffield Island?

Yes, there are holiday rentals close to the most popular sights in Sheffield Island, or you can select a more secluded option if you're looking for a relaxing stay. Sheffield Island is known for its monuments.

What are some of the best holiday rentals that Sheffield Island has to offer?

Business or Weekend escape: This holiday home rental outside of Sheffield Island offers a garden, a BBQ 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 wider area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a holiday rental in Sheffield Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheffield Island. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.