Sheffield Island Vacation Rentals

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Our top choices for Sheffield Island vacation rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is CA $116
CA $200 total
includes taxes & fees
Mar 1 - Mar 2
Business or Weekend escape

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is CA $145
CA $396 total
includes taxes & fees
Feb 13 - Feb 14
Renovated 2BR Retreat / Modern Comforts Included

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
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is CA $167
CA $285 total
includes taxes & fees
Feb 10 - Feb 11
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is CA $163
CA $390 total
includes taxes & fees
Mar 2 - Mar 3
Luxury 3BR Home Game Room Free Parking

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay here. The rooms are clean and comfortable. The hosts are very friendly and hospitable."
United States
Joseph M.
The price is CA $146
CA $328 total
includes taxes & fees
Feb 16 - Feb 17
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is CA $170
CA $431 total
includes taxes & fees
Feb 10 - Feb 11
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is CA $185
CA $556 total
includes taxes & fees
Feb 10 - Feb 11
Luxury Designer 2 bedroom+office/3bed vacation home.

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, (18 reviews)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is CA $170
CA $249 total
includes taxes & fees
Feb 10 - Feb 11
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful "
United States
Nolufefe Z.
The price is CA $185
CA $484 total
includes taxes & fees
Feb 10 - Feb 11
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is CA $145
CA $398 total
includes taxes & fees
Feb 10 - Feb 11
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is CA $181
CA $524 total
includes taxes & fees
Feb 10 - Feb 11
Marine Theme - 4 BR - Backyard - Fire pit

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $215
CA $454 total
includes taxes & fees
Feb 17 - Feb 18
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is CA $150
CA $376 total
includes taxes & fees
Feb 10 - Feb 11
Elegant Hideaway with Free Parking

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
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is CA $215
CA $409 total
includes taxes & fees
Feb 10 - Feb 11
Centric property close to all the great things in the city

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is CA $276
CA $644 total
includes taxes & fees
Feb 11 - Feb 12
Captain's Cottage - Cold Spring Harbor Water Views

Cozy Cottage with Fire Pit, near Beach

Cozy Cottage with Fire Pit, near Beach
Fairfield
10.0 out of 10, Exceptional, (27 reviews)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is CA $245
CA $667 total
includes taxes & fees
Feb 10 - Feb 11
Cozy Cottage with Fire Pit, near Beach

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is CA $342
CA $667 total
includes taxes & fees
Feb 28 - Mar 1
THE OASIS @ LONG ISLAND

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, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is CA $203
CA $526 total
includes taxes & fees
Feb 10 - Feb 11
Seabreeze at the beach west beach Stamford ct.

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is CA $615
CA $930 total
includes taxes & fees
Feb 11 - Feb 12
Luxury NYC Home with Free Parking for 12
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?

Beautiful historic home in Stony Brook!: This vacation home rental outside of Sheffield Island has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.