Photo by Richard Miska

Sheffield Island Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sheffield Island holiday rentals

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is NZ$219
includes taxes & fees
4 Jan - 5 Jan 2026
Stamford Suites

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is NZ$163
includes taxes & fees
24 Jan - 25 Jan 2026
The Mansion Hotel-style

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$547
includes taxes & fees
2 Jan - 3 Jan 2026
Guesthouse at Norwalk Inn

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"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 NZ$495
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (1)
"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 NZ$539
includes taxes & fees
27 Jan - 28 Jan 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
4.0 star property
The price is NZ$1,166
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury NYC Home with Free Parking for 12

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"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 NZ$763
includes taxes & fees
31 Dec - 1 Jan 2026
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (8)
"The apartment was very clean with everything we needed for our stay. Outside noise was a little loud so I’d suggest a sound machine, but in case your forget the awesome host has supplied soft ear plugs for you. I would definitely visit again. "
United States
Chrystie
The price is NZ$394
includes taxes & fees
14 Jan - 15 Jan 2026
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Holiday Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is NZ$251
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
The price is NZ$646
includes taxes & fees
6 Jan - 7 Jan 2026
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
9.4 out of 10, Exceptional, (12)
"This location is great close to highway and mall."
United States
Sansia D.
Updated, cozy single family in Fairfield County
9.6 out of 10, Exceptional, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is NZ$427
includes taxes & fees
1 Jan - 2 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
8.0 out of 10, Very good, (1)
"It was clean "
United States
Burton
The price is NZ$495
includes taxes & fees
4 Jan - 5 Jan 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
10.0 out of 10, Exceptional, (11)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is NZ$823
includes taxes & fees
19 Jan - 20 Jan 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach
10.0 out of 10, Exceptional, (16)
"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 NZ$313
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
9.4 out of 10, Exceptional, (20)
"Very nice house and location. Very good service and excellent attention."
Mexico
Armando V.
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
10.0 out of 10, Exceptional, (23)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is NZ$826
includes taxes & fees
19 Jan - 20 Jan 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is NZ$786
includes taxes & fees
27 Jan - 28 Jan 2026
Marine Theme - 4 BR - Backyard - Fire pit
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is NZ$658
includes taxes & fees
27 Jan - 28 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 NZ$219 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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Sheffield Island is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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.