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Sheffield Island Vacation Rentals

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Our top choices for Sheffield Island vacation 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 CA $301
CA $347 total
includes taxes & fees
Aug 27 - Aug 28
Guesthouse at Norwalk Inn

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (110 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $243
CA $363 total
includes taxes & fees
Sep 13 - Sep 14
DUNE Fairfield Beach

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (166 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is CA $185
CA $213 total
includes taxes & fees
Aug 30 - Aug 31
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 CA $198
CA $432 total
includes taxes & fees
Sep 5 - Sep 6
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

5. 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 CA $117
CA $225 total
includes taxes & fees
Aug 26 - Aug 27
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

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 CA $195
CA $368 total
includes taxes & fees
Aug 26 - Aug 27
Spacious Studio with Pool Table

7. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
The price is CA $233
CA $372 total
includes taxes & fees
Sep 3 - Sep 4
Modern Apartment with Private Entrance

8. 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 CA $186
CA $380 total
includes taxes & fees
Aug 27 - Aug 28
Romantic Hide Out

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 CA $269
CA $520 total
includes taxes & fees
Sep 8 - Sep 9
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10. 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 CA $198
CA $572 total
includes taxes & fees
Sep 5 - Sep 6
Modern Luxe 1BR Apt in Downtown Stamford

11. 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 CA $274
CA $495 total
includes taxes & fees
Aug 30 - Aug 31
Modern Luxury 1BR Stamford Getaway

12. 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 CA $384
CA $495 total
includes taxes & fees
Aug 30 - Aug 31
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

13. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is CA $322
CA $592 total
includes taxes & fees
Sep 14 - Sep 15
Gilded Age Luxury Surrounded by Nature

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, (26 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is CA $167
CA $246 total
includes taxes & fees
Aug 26 - Aug 27
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

15. 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)
"Great place to stay with a friendly and responsive host! Loved that it was also pet and kid-friendly! "
United States
Chelsea P.
The price is CA $324
CA $774 total
includes taxes & fees
Sep 21 - Sep 22
Seabreeze at the beach west beach Stamford ct.

16. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cozy get away"
United States
Anonymous traveller
The price is CA $186
CA $461 total
includes taxes & fees
Aug 26 - Aug 27
Modern 2 Bed in BlackRock

17. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is CA $372
CA $478 total
includes taxes & fees
Aug 29 - Aug 30
2-bedroom apartmet No cleaning Fee

18. 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 CA $424
CA $982 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Retreat with Game Room and Fire Pit

19. 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 CA $473
CA $1,052 total
includes taxes & fees
Sep 14 - Sep 15
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

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, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is CA $323
CA $559 total
includes taxes & fees
Sep 15 - Sep 16
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

Find out more about Sheffield Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sheffield Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Charming Home in Seaside: This vacation home rental outside of Sheffield Island is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.