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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
The price is CA $495
CA $570 total
includes taxes & fees
Oct 19 - Oct 20
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, (189 reviews)
The price is CA $205
CA $236 total
includes taxes & fees
Oct 13 - Oct 14
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, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $252
CA $377 total
includes taxes & fees
Oct 19 - Oct 20
DUNE Fairfield Beach
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (18 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is CA $356
CA $702 total
includes taxes & fees
Oct 18 - Oct 19
Nama-stay, sweet pink Saugatuck Shores beach cottage
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

5. 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 $205
CA $597 total
includes taxes & fees
Oct 15 - Oct 16
Modern Luxe 1BR Apt in Downtown Stamford
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

6. 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, (17 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is CA $315
CA $775 total
includes taxes & fees
Nov 3 - Nov 4
Seabreeze at the beach west beach Stamford ct.
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

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, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is CA $224
CA $470 total
includes taxes & fees
Oct 14 - Oct 15
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

8. 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 CA $407
CA $1,026 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach Home | Walk to Cove Beach + Private Yard
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

9. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is CA $333
CA $610 total
includes taxes & fees
Oct 13 - Oct 14
Gilded Age Luxury Surrounded by Nature
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.

10. 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, (31 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 CA $681
CA $1,368 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern living room with a sofa, a coffee table, and a bar stool.

11. 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 $205
CA $449 total
includes taxes & fees
Oct 18 - Oct 19
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

12. 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 $236
CA $427 total
includes taxes & fees
Oct 20 - Oct 21
Spacious Studio with Pool Table
A living room with a sofa set, a coffee table, and a television on a stand.

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 CA $467
CA $891 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Stamford Home | Family, Work, Parking
Open concept kitchen

14. 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)
The price is CA $741
CA $1,529 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach House, Game Room + Huge Backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

15. 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.
The price is CA $494
CA $951 total
includes taxes & fees
Oct 28 - Oct 29
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A modern kitchen with a central island, pendant lights, and built-in shelves.

16. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is CA $290
CA $439 total
includes taxes & fees
Nov 1 - Nov 2
Stylish Home With Free ParkingZA
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

17. 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 $403
CA $980 total
includes taxes & fees
Nov 9 - Nov 10
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A campfire with a wooden table and benches by a lake.

18. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is CA $243
CA $497 total
includes taxes & fees
Oct 11 - Oct 12
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with white cabinets, a marble island, and black bar stools.

19. 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 CA $542
CA $1,160 total
includes taxes & fees
Oct 28 - Oct 29
Spacious Retreat with Game Room and Fire Pit
A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

20. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
The price is CA $227
CA $421 total
includes taxes & fees
Oct 11 - Oct 12
Modern Apartment with Private Entrance
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

J House Greenwich

J House Greenwich

10/10 Excellent
"Rooms were clean, check- in was easy Staff was excellent , breakfast was great Tony’s restaurant was over the top so was Tony!! Over all great experience Would definitely stay again"
Sarah 1-night trip
Posted 1 hour ago
J House Greenwich

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield Island vacation rentals we have selected for you start as low as CA $217 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 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. 

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.