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Winton Vacation Rentals

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Our top choices for Winton vacation rentals

3.5 star property
9.8 out of 10, Exceptional, (38)
"Excellent stay, very comfortable and easy to find. Would stay again. "
United Kingdom
Iain
$126 nightly
The price is $151
Jan 2 - Jan 3, 2026
Total with taxes and fees
Milton House Studio Apartment Suites

Cottage in Appleby-in-Westmorland

Cosy Nook Cottage
3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing property. It fits our needs and my toddler son loved exploring the cottage! Very cosy."
United Kingdom
Anonymous traveler
$186 nightly
The price is $223
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cosy Nook Cottage

Cottage in Leyburn

River Dance Cottage
3.0 star property
10.0 out of 10, Exceptional, (3)
"Great cosy cottage in a fantastic location. Definitely recommend "
United Kingdom
Adam
River Dance Cottage

Cottage in Barnard Castle

Cobblers Barn
3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was absolutely lovely, clean, warm and inviting "
United Kingdom
Jackie
$1,100 nightly
The price is $1,320
Jan 2 - Jan 3, 2026
Total with taxes and fees
Cobblers Barn

Cottage in Appleby-in-Westmorland

The New Inn 1730
3.5 star property
5.0 out of 10, (2)
"Our stay at the New Inn 1730 was only overnight, and we arrived around 6pm on a Sunday evening. This is a welcoming & friendly pub, with restaurant and accommodation. The owner did his best to accommodate our needs during our short stay, and is still finding his feet a little having only recently taken on the business. Food options were limited when we arrived, particularly for our two fussy children, so we did eat elsewhere that night, but the cooked breakfast in the morning was very good,...
United Kingdom
Malcolm
$157 nightly
The price is $189
Jan 2 - Jan 3, 2026
Total with taxes and fees
The New Inn 1730

Cottage in Leyburn

Flanders Hall
3.5 star property
$2,011 nightly
The price is $2,011
Jan 5 - Jan 6, 2026
Total with taxes and fees
Flanders Hall

Cottage in Kirkby Stephen

Cherry Tree Cottage
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful cottage in a quite location."
United Kingdom
Mrs Susan
$296 nightly
The price is $355
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cherry Tree Cottage

Cottage in Penrith

The Cobbles
3.5 star property
10.0 out of 10, Exceptional, (1)
"Stayed at The Cobbles many times, never disappoints."
United Kingdom
Susan
$336 nightly
The price is $403
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Cobbles

Cottage in Appleby-in-Westmorland

Chapel Cottage
3.5 star property
10.0 out of 10, Exceptional, (1)
"Very nice stay. Great experience, very comfortable, and good size of a family of four. Very good location. Lots of places to see in the area. Very nice welcome pack. Thanks. "
United Kingdom
J
$361 nightly
The price is $434
Jan 3 - Jan 4, 2026
Total with taxes and fees
Chapel Cottage

Cottage in Leyburn

Hall Garth Cottage
3.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect. Wondetful home.in the perfect setting"
United Kingdom
Joanne
$463 nightly
The price is $556
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hall Garth Cottage

Cottage in Sedbergh

3 Mountain View
2.5 star property
10.0 out of 10, Exceptional, (1)
"The property is a delightful 19th century cottage. The views are incredible. The property owner goes above and beyond in what she provides. We will be back. "
United Kingdom
Jean
$380 nightly
The price is $456
Jan 3 - Jan 4, 2026
Total with taxes and fees
3 Mountain View

Cottage in Barnard Castle

Heatherbrae
3.0 star property
$3,693 nightly
The price is $4,432
Jan 5 - Jan 6, 2026
Total with taxes and fees
Heatherbrae

Cottage in Penrith

21 Eamont Park
3.5 star property
$306 nightly
The price is $368
Jan 3 - Jan 4, 2026
Total with taxes and fees
21 Eamont Park

Cottage in Barnard Castle

Low Shipley Cottage
3.5 star property
$472 nightly
The price is $566
Jan 5 - Jan 6, 2026
Total with taxes and fees
Low Shipley Cottage

Cottage in Sedbergh

Fells Cottage
3.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was clean. The modern kitchen offered everything that we needed. The living room was small but cosy with the log burner. The staff satisfied our request with a baby high chair (a travel cot was also possible but we did not need it). The only issue for us was the shower which was not very powerful."
United Kingdom
Clémentine
$367 nightly
The price is $441
Jan 5 - Jan 6, 2026
Total with taxes and fees
Fells Cottage

Cottage in Appleby-in-Westmorland

Dunfell Shepherd's Hut
3.0 star property
8.0 out of 10, Very Good, (1)
"This is a beautifully appointed shepherd's hut on the edge of a pretty and quiet village in the North Pennines. Lots of walking routes nearby and just a few miles from Appleby-in-Westmoreland. We enjoyed our stay very much though were disappointed that the internet signal was so poor. The TV would not stream smoothly so not worth having it there at the moment. Still, this was a small sacrifice for the pleasure of experiencing tiny living life for a few days. Everything else worked really...
United Kingdom
Mary
$349 nightly
The price is $419
Jan 3 - Jan 4, 2026
Total with taxes and fees
Dunfell Shepherd's Hut

Cottage in Kirkby Stephen

Corner Cottage
3.0 star property
9.0 out of 10, Wonderful, (2)
"Cosy cottage, very comfy bed, well equipped. Lovely area of the country, many walks from the property."
United Kingdom
Anonymous traveler
$305 nightly
The price is $366
Jan 2 - Jan 3, 2026
Total with taxes and fees
Corner Cottage

Cottage in Richmond

Padley Barn
3.0 star property
$393 nightly
The price is $471
Jan 24 - Jan 25, 2026
Total with taxes and fees
Padley Barn

Cottage in Skipton

Dale Head Cottage
3.5 star property
$358 nightly
The price is $430
Jan 10 - Jan 11, 2026
Total with taxes and fees
Dale Head Cottage

Cottage in Barnard Castle

Cedar Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
$489 nightly
The price is $586
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cedar Cottage
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 Winton Hotel Reviews

Find out more about Winton

Everything you need to know about Winton 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 Winton 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 Winton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winton. 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 Winton 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 $151 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 Winton rentals

At Expedia, we put the best Winton 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 Winton 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 Winton 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 Winton. 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 Winton?

Yes, you can find vacation rentals close to popular sights in Winton, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winton has to offer?

Luxury Barn Conversion - Orchard View: Visitors like this Winton vacation home rental. It is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

What can I see and do in Winton?

Yorkshire Dales National Park and Eden Valley are a couple of scenic spots to enjoy the outdoors, whereas Swaledale Museum is one of the cultural attractions. North Pennines and Buttertubs Pass are a couple of places you'll find in the larger area.

What are vacation rentals like in Winton?

Vacation rentals are private properties you can reserve for several days or more in Winton. Vacation rentals offer extras like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.