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Holiday Rentals in Winton

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Our top choices for Winton holiday rentals

Milton House Studio Apartment Suites

Milton House Studio Apartment Suites
3.5 star property
Leyburn
9.8 out of 10, Exceptional, (38)
"Excellent stay, very comfortable and easy to find. Would stay again. "
United Kingdom
Iain
The price is €128
includes taxes & fees
16 Jan - 17 Jan 2026
Milton House Studio Apartment Suites

Cosy Nook Cottage

Cosy Nook Cottage
3.0 star property
Appleby-in-Westmorland
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 traveller
The price is €189
includes taxes & fees
8 Jan - 9 Jan 2026
Cosy Nook Cottage

River Dance Cottage

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

Cobblers Barn

Cobblers Barn
3.0 star property
Barnard Castle
10.0 out of 10, Exceptional, (1)
"Property was absolutely lovely, clean, warm and inviting "
United Kingdom
Jackie
The price is €1,153
includes taxes & fees
4 Jan - 5 Jan 2026
Cobblers Barn

The New Inn 1730

The New Inn 1730
3.5 star property
Appleby-in-Westmorland
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
The price is €161
includes taxes & fees
2 Jan - 3 Jan 2026
The New Inn 1730

Flanders Hall

Flanders Hall
3.5 star property
Leyburn
The price is €1,710
includes taxes & fees
5 Jan - 6 Jan 2026
Flanders Hall

Cherry Tree Cottage

Cherry Tree Cottage
2.0 star property
Kirkby Stephen
10.0 out of 10, Exceptional, (1)
"Beautiful cottage in a quite location."
United Kingdom
Mrs Susan
The price is €302
includes taxes & fees
3 Jan - 4 Jan 2026
Cherry Tree Cottage

The Cobbles

The Cobbles
3.5 star property
Penrith
10.0 out of 10, Exceptional, (1)
"Stayed at The Cobbles many times, never disappoints."
United Kingdom
Susan
The price is €343
includes taxes & fees
3 Jan - 4 Jan 2026
The Cobbles

Chapel Cottage

Chapel Cottage
3.5 star property
Appleby-in-Westmorland
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
The price is €369
includes taxes & fees
3 Jan - 4 Jan 2026
Chapel Cottage

Hall Garth Cottage

Hall Garth Cottage
3.0 star property
Leyburn
10.0 out of 10, Exceptional, (2)
"Perfect. Wondetful home.in the perfect setting"
United Kingdom
Joanne
The price is €546
includes taxes & fees
5 Jan - 6 Jan 2026
Hall Garth Cottage

3 Mountain View

3 Mountain View
2.5 star property
Sedbergh
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
The price is €387
includes taxes & fees
3 Jan - 4 Jan 2026
3 Mountain View

Heatherbrae

Heatherbrae
3.0 star property
Barnard Castle
The price is €3,768
includes taxes & fees
5 Jan - 6 Jan 2026
Heatherbrae

21 Eamont Park

21 Eamont Park
3.5 star property
Penrith
The price is €313
includes taxes & fees
3 Jan - 4 Jan 2026
21 Eamont Park

Low Shipley Cottage

Low Shipley Cottage
3.5 star property
Barnard Castle
The price is €481
includes taxes & fees
5 Jan - 6 Jan 2026
Low Shipley Cottage

Fells Cottage

Fells Cottage
3.0 star property
Sedbergh
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
The price is €374
includes taxes & fees
5 Jan - 6 Jan 2026
Fells Cottage

Dunfell Shepherd's Hut

Dunfell Shepherd's Hut
3.0 star property
Appleby-in-Westmorland
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
The price is €365
includes taxes & fees
4 Jan - 5 Jan 2026
Dunfell Shepherd's Hut

Corner Cottage

Corner Cottage
3.0 star property
Kirkby Stephen
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 traveller
Corner Cottage

Padley Barn

Padley Barn
3.0 star property
Richmond
Padley Barn

Dale Head Cottage

Dale Head Cottage
3.5 star property
Skipton
The price is €365
includes taxes & fees
10 Jan - 11 Jan 2026
Dale Head Cottage

Cedar Cottage

Cedar Cottage
3.0 star property
Barnard Castle
10.0 out of 10, Exceptional, (1)
The price is €499
includes taxes & fees
11 Jan - 12 Jan 2026
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 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 Winton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Winton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winton holiday 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 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 Winton 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 Winton holiday rentals we have selected for you start as low as €128 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winton rentals

At Expedia, we put the best Winton 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 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 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 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. 

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Winton?

Yes, there are holiday rentals close to the most popular sights in Winton, or you can select a more secluded option if you're looking for a relaxing stay.

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

Luxury Barn Conversion - Orchard View: This holiday home rental outside of Winton is located in a rural location, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Make the most of 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 wider area.

What are holiday rentals like in Winton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winton. Holiday rentals offer amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.