A stone lighthouse with a white tower and black lantern room, surrounded by greenery and a clear blue sky.

Sheffield Island Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$219 nightly
The price is $252
Sep 1 - Sep 2
Total with taxes and fees
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, (170 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$164 nightly
The price is $189
Sep 3 - Sep 4
Total with taxes and fees
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, (111 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$233 nightly
The price is $268
Sep 21 - Sep 22
Total with taxes and fees
DUNE Fairfield Beach
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

4. 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.
$609 nightly
The price is $690
Sep 3 - Sep 4
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

5. 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.
$387 nightly
The price is $438
Sep 1 - Sep 2
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

6. 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.
$613 nightly
The price is $694
Sep 23 - Sep 24
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage

7. 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)
"Great stay!"
United States
Kyra S.
$830 nightly
The price is $881
Sep 2 - Sep 3
Total with taxes and fees
5BR Beach House, Game Room + Huge Backyard
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.

8. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
$863 nightly
The price is $916
Sep 22 - Sep 23
Total with taxes and fees
5BR Beach House, Water Views, Game Room, Backyard

9. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$382 nightly
The price is $432
Sep 8 - Sep 9
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

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.
$370 nightly
The price is $419
Sep 5 - Sep 6
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

11. 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.
$335 nightly
The price is $378
Sep 28 - Sep 29
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A living room with a sofa set, a coffee table, and a television on a stand.

12. 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.
$520 nightly
The price is $588
Sep 3 - Sep 4
Total with taxes and fees
Spacious Stamford Home | Family, Work, Parking
A modern living room with a large window offering a cityscape view, a blue sofa, a small side table, and a flat-screen TV.

13. The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Cove - East Side - Shippan
9.0 out of 10, Wonderful, (10 reviews)
"Beautiful place, very clean. Great Host!"
United States
Alejandro A.
$919 nightly
The price is $1,043
Sep 7 - Sep 8
Total with taxes and fees
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

14. 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, (17 reviews)
"Great place to stay with a friendly and responsive host! Loved that it was also pet and kid-friendly! "
United States
Chelsea P.
$489 nightly
The price is $553
Sep 29 - Sep 30
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
A modern kitchen with white cabinets, a marble island, and black bar stools.

15. 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.
$683 nightly
The price is $773
Sep 16 - Sep 17
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

16. 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.
$318 nightly
The price is $360
Sep 1 - Sep 2
Total with taxes and fees
Modern Luxury 1BR Stamford Getaway
A bedroom with a bed, a round mirror, a door, and wall decorations.

17. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
$307 nightly
The price is $348
Sep 7 - Sep 8
Total with taxes and fees
2-bedroom apartmet No cleaning Fee

18. 4 BR VILLA, celebration welcome, No Cleaning fee

4 BR VILLA, celebration welcome, No Cleaning fee
West Norwalk
$663 nightly
The price is $751
Sep 7 - Sep 8
Total with taxes and fees
4 BR VILLA, celebration welcome, No Cleaning fee
A living room with a piano, a white sofa, a coffee table, and a lamp.

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

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 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.
$633 nightly
The price is $716
Sep 14 - Sep 15
Total with taxes and fees
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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

10/10 Excellent
"Very clean and modern"
Bethany 1-night trip
Posted 5 hours ago
EVEN Hotel Norwalk by IHG

Find out more about Sheffield Island

Everything you need to know about Sheffield Island vacation rentals

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

Sheffield Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sheffield Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheffield Island rentals

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

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.

Explore a world of travel with Expedia

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.