Photo by Richard Miska

Sheffield Island Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Sheffield Island

Stamford Suites
2.5 star property
6.8 out of 10, 715 reviews
"Not a bad stay overall. Nice location opposite the police headquarters and courthouse. Friendly staff. Brianna the hostess was very nice. The suite was very large. The only thing is that the carpet needs changing. The continental breakfast wasn't appetizing but there's food all around the area. But all in all it was an enjoyable stay."
The price is NZ$286
per night
16 Jun - 17 Jun
Stamford Suites
Business or Weekend escape
9.8 out of 10, Exceptional, 11 reviews
"The place was clean. Very comfortable. He had refreshments in the fridge. 2nd time here. The host is very easy to get to answer from. We are coming back again soon."
The price is NZ$230
per night
12 Jun - 13 Jun
Business or Weekend escape
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, 10 reviews
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is NZ$383
per night
4 Jun - 5 Jun
DUNE Fairfield Beach
Save an average of 15% on thousands of hotels when you're signed in
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, 104 reviews
"Neighborhood great for walking dogs. Would have loved a sink besides bathroom. Overall great value."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, 9 reviews
"Beautiful spacious apartment with everything you would need for a comfortable stay. Quick responses to our questions by owners. An easy and convenient location just a short drive to visit our daughter at nearby University. Highly recommend this apartment. "
The price is NZ$670
per night
2 Jun - 3 Jun
Luxury Designer 2 bedroom+office/3bed vacation home.
Global Luxury Suites White Plains
3.5 star property
7.6 out of 10, Good, 17 reviews
"If this option is available in the city you are traveling to, take it! You get a home-y, modern APARTMENT with space, rather than a tiny, old hotel room. I always search Global Luxury Suites before searching anything else."
Global Luxury Suites White Plains
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
The price is NZ$731
per night
1 Jun - 2 Jun
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, 15 reviews
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, 14 reviews
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is NZ$1,374
per night
1 Jun - 2 Jun
Westport Paradise With Every Amenity!
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
10.0 out of 10, Exceptional, 2 reviews
"Amazing place to stay people are great"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 17 reviews
"My husband, dog and I had a great Memorial Day weekend at this lakeside property. The house is a short drive away from NYC and is situated perfectly between the quaint towns of Ridgefield and Katonah. We had a good time enjoying the lake and nearby hikes."
Serenity Awaits at this Cozy Lakeside Bungalow
Luxury penthouse suite
2.0 out of 10, 1 review
"it had roaches"
The price is NZ$605
per night
1 Jun - 2 Jun
Luxury penthouse suite
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, 12 reviews
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
The Safe House - High Tech Apt #2 - 3 Beds
10.0 out of 10, Exceptional, 29 reviews
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The Safe House - High Tech Apt #2 - 3 Beds
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
10.0 out of 10, Exceptional, 7 reviews
"GREAT location and house for a family reunion. It had everything that we needed inside and out. Large rooms for entertaining, a beautiful pool and outdoor patio. Very centrally located for shopping, airports, farm stands and yet very quiet. GREAT STAY!"
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, 13 reviews
"This was walking distance to the Total Mortgage Arena for our robotics competition. Having the full kitchen to cook meals was awesome. Nice comfy beds, plenty of space, I claimed the nook off the kitchen/dining area for myself. Boys had front room to work on their robot."
Cheerful 4 bedrooms residential house.
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, 37 reviews
"The pictures are very deceiving - as they are of the Guesthouses not the main hotel. I thought I was booking at an Inn, but I was really booked at a regular ole chain hotel. One that charges $8 per person per day for their pool! (you should really change this policy for paying overnight guests - why should we pay additional for facilities like this?) There's also nowhere to walk to from here, so if you're without a car expect to be paying for Ubers everywhere (which is fine as they're readily...
The price is NZ$477
per night
1 Jul - 2 Jul
Guesthouse at Norwalk Inn
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, 3 reviews
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is NZ$437
per night
30 Jun - 1 Jul
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, 11 reviews
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
The price is NZ$499
per night
5 Jun - 6 Jun
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Don't see what you're looking for?
See all available properties in Sheffield Island
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.

Other types of properties in Sheffield Island you may be interested in

East Norwich Inn
2.5 star property
7.8 out of 10, Good, 1,722 reviews
"Our fav place to go for peace and quiet and quality time away from children and family."
The price is NZ$228
per night
3 Jun - 4 Jun
East Norwich Inn
Radisson Hotel Hauppauge-Long Island
3.5 star property
6.0 out of 10, 1,005 reviews
"Should have a free breakfast for the price they charged. "
The price is NZ$220
per night
23 Jun - 24 Jun
Radisson Hotel Hauppauge-Long Island
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, 1,505 reviews
"Very comfortable stay with friendly and helpful staff."
The price is NZ$190
per night
2 Jun - 3 Jun
Amsterdam Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sheffield Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sheffield Island. 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 Sheffield Island. 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 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 holiday 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 Sheffield Island short-term rentals, that won’t be hard to do.

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?

Business or Weekend escape: This holiday home rental outside of Sheffield Island has air conditioning and WiFi 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 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.

Recent reviews of Sheffield Island properties
Expedia verified reviews