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Sheffield Island Vacation Rentals

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Vacation Rentals in Sheffield Island

Stamford Suites
2.5 star property
6.8 out of 10, 719 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 $169
$195 total
includes taxes & fees
Jun 11 - Jun 12
Stamford Suites
Business or Weekend escape
9.6 out of 10, Exceptional, 12 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 $80
$141 total
includes taxes & fees
Jun 10 - Jun 11
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 $210
$297 total
includes taxes & fees
Jun 10 - Jun 11
DUNE Fairfield Beach
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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, 10 reviews
"Had a great stay!"
The price is $128
$397 total
includes taxes & fees
Jun 24 - Jun 25
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.
10.0 out of 10, Exceptional, 1 review
"Great location and great house. Didn't understand why we couldn't flush toilet paper in master bathroom. Otherwise everything was great."
The price is $300
$449 total
includes taxes & fees
Jun 9 - Jun 10
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
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 $585
$841 total
includes taxes & fees
Jun 7 - Jun 8
Westport Paradise With Every Amenity!
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
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 18 reviews
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
Luxury penthouse suite
2.0 out of 10, 1 review
"it had roaches"
The price is $250
$370 total
includes taxes & fees
Jun 6 - Jun 7
Luxury penthouse suite
(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
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
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 $226
$260 total
includes taxes & fees
Jun 19 - Jun 20
Guesthouse at Norwalk Inn
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
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
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
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.
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 $150
$268 total
includes taxes & fees
Jun 30 - Jul 1
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
The price is $221
$307 total
includes taxes & fees
Jun 11 - Jun 12
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, 1,736 reviews
"You walk in and its a pretty hotel, nicely decorated. But as you go down to your room, its very dated. The decor in the room is dated and my pillow was too firm. However, the staff was friendly, the room was clean and it was in a quiet area. The bed was comfortable but im glad i brought my own pillow. I would stay here again "
The price is $108
$121 total
includes taxes & fees
Jun 12 - Jun 13
East Norwich Inn
Radisson Hotel Hauppauge-Long Island
3.5 star property
6.0 out of 10, 1,007 reviews
"Should have a free breakfast for the price they charged. "
The price is $118
$142 total
includes taxes & fees
Jun 23 - Jun 24
Radisson Hotel Hauppauge-Long Island
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very Good, 1,519 reviews
"Good value. Very clean. Very nice staff. The room is outdated. Beds were too soft not too comfortable. AC worked well but was loud when it kicked on. I would definitely recommend this property if you need a clean , friendly place to stay for a good price."
The price is $90
$105 total
includes taxes & fees
Jun 18 - Jun 19
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.

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 $80 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.

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?

Business or Weekend escape: This vacation 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 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.

Recent reviews of Sheffield Island properties
Expedia verified reviews