Winton Vacation Rentals from CA $308: Short-Term Rentals for 2026

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Our top choices for Winton vacation rentals

1. Muddy Boots – Scarpa.

Kirkby Stephen

Louise J.

CA $327 total

includes taxes & fees

Sep 13 - Sep 14

A bedroom with a stone wall, two bedside tables with lamps, a bed with a fur rug, and two towels on the bed.

2. Muddy Boots - Arcade Royale

Kirkby Stephen

CA $327 total

includes taxes & fees

Sep 14 - Sep 15

A stone building with a large window, a bench, and a potted plant.

3. Cosy Nook Cottage

Appleby-in-Westmorland

Anonymous traveller

CA $345 total

includes taxes & fees

Sep 29 - Sep 30

A cozy room with a kitchen, a sofa, a dining area, and a large sliding glass door leading to a balcony.

4. The Elm Shepod - Smardale Mill - Modern cosy glamping pod with amazing views, Sleeps 4 guests in 1 b

Kirkby Stephen

kirstine R.

CA $318 total

includes taxes & fees

Sep 14 - Sep 15

A stone patio with a table and chairs, a stone wall, and a tree.

5. Cherry Tree Cottage

Kirkby Stephen

Gwyn

CA $504 total

includes taxes & fees

Oct 5 - Oct 6

6. The Ash Shepod - Smardale Mill - Fabulous glamping pod/shepherds hut, sleeps 4 guests in 1 room

Kirkby Stephen

Dominic C.

CA $318 total

includes taxes & fees

Sep 14 - Sep 15

A bed with a metal frame, a bedside table with a lamp, and a window with a view of greenery.

7. A spacious detached cottage located by a beck in a quiet village.

Hartley, Kirkby Stephen

Judith Cavanagh

CA $902 total

includes taxes & fees

Sep 22 - Sep 23

A room with a view of a stone wall and a wooden deck.

8. 3 bedroom accommodation in Newbiggin on Lune, near Kirkby Stephen

Newbiggin on Lune, near Kirkby Stephen

Tracy Davies

CA $405 total

includes taxes & fees

Sep 24 - Sep 25

A cozy log cabin interior with a fireplace, a sofa, a chair, and a wooden ceiling.

9. Curlew Lodge - sleeps 6 guests in 3 bedrooms

Ravenstonedale / Kirkby Stephen

"We all had the most wonderful New Year stay at Curlew Lodge, it was spotless with some lovely personal touches such as fresh bread, eggs, butter & a chocolate cake that was delicious! The garden & views were lovely. The weather was terrible for most of our stay so didn’t manage to explore as much as we’d have have liked. The local village was a 25 min walk, we enjoyed a few visits to the Kings Head which was lovely with good food & atmosphere. We look forward to going back again. The only...

Mrs hannah Patterson P.

A stone building with a wooden door and windows. There are potted plants and flowers on the steps.

10. Cosy 2 bed-room cottage near High Force Waterfall

Middleton-in-Teesdale

Julie N.

CA $297 total

includes taxes & fees

Sep 16 - Sep 17

A living room with a fireplace, a television mounted on the wall, and a sofa with cushions.

11. 1 bedroom accommodation in Appleby-in-Westmorland

Appleby-in-Westmorland

Andrew D.

CA $536 total

includes taxes & fees

Sep 26 - Sep 27

A stone building with a traditional design, featuring a small garden area with plants and a stone wall.

12. Howgills Apartment 7 (self-catering accommodation with free parking and Wi-Fi)

Sedbergh

lauren w.

CA $510 total

includes taxes & fees

Sep 17 - Sep 18

A conservatory with wicker furniture, a laptop, and a vase of flowers.

13. 2 bedroom accommodation in Barnard Castle

Barnard Castle

"Spent a lovely week at Ashlea Country Cottage, Ann, the owner was so nice and helpful, made us feel right at home from the moment we arrived. This is a lovely cosy cottage set in beautiful peaceful surroundings. We even got real thick snow which was an added bonus, great to watch surrounding wildlife and had visits from sheep. The wood burner was a real hit, made the cottage feel homely and warm, great place to explore from and the fresh warm bread on arrival was an absolute bonus. We will be...

Stephen Bamber

CA $462 total

includes taxes & fees

Sep 29 - Sep 30

14. Studio flat, views of Whernside , perfect base for exploring the Yorkshire dales

Deepdale

"comfortable clean cozy and very tidy, with great views across the valley to Whernside, wish we could have stayed longer maybe next time, The kitchen was well maintained and had all you needed, the bed was comfortable and the shower was great. The dark night was amazing coming from a town we dont see dark like that! Glad we taken our SUV and not the hatchback as we would have struggled on the bumpy roads due to its very low front end."

Ian B.

CA $165 total

includes taxes & fees

Sep 15 - Sep 16

A carpeted staircase with white balusters, a plain wall, and a window with a curtain.

15. Burn Bank

Appleby-in-Westmorland

CA $516 total

includes taxes & fees

Sep 19 - Sep 20

A modern kitchen with grey cabinets, a built-in oven, and a window providing natural light.

16. A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.

Richmond

Diana v.

CA $705 total

includes taxes & fees

Sep 18 - Sep 19

A stone cottage with a black metal fence, a sign reading "Ivy Cottage," and a small garden area.

17. High-quality bolthole and cosy sanctuary for 2 people in a picturesque village location with WiFi.

Richmond

Victoria

CA $744 total

includes taxes & fees

Sep 21 - Sep 22

A stone building with a paved patio, a bench, and a table with chairs.

18. River Dance Cottage

Leyburn

Adam

CA $412 total

includes taxes & fees

Sep 10 - Sep 11

A double bed with two nightstands, a window with a view, and decorative pillows.

19. Howgills Apartment 11 (self-catering accommodation with free parking and Wi-Fi)

Sedbergh

lauren w.

CA $589 total

includes taxes & fees

Sep 17 - Sep 18

A scenic view from a balcony with a metal railing, overlooking a grassy field with trees and a stone wall.

20. The Yorkshire Dales Snug - Walkers' Delight - Pet Friendly

Buckden

Janette

CA $233 total

includes taxes & fees

Sep 13 - Sep 14

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Top Winton Hotel Reviews

Shap Wells Hotel

10/10 Excellent

"A great overnight stop en route to Scotland. Wonderfully peaceful location with great walks around the hotel grounds. As others have mentioned do not take the direct sat nav guided route when you first leave the motorway. Follow the road to the A6 and enter from that direction otherwise you will be negotiating large potholes coming in the back way."

The Charles Bathurst Inn

10/10 Excellent

"This is an excellent place to stay. The food is very good indeed. We booked last minute, risking what the building was like. We don't like lots of stairs and there are lots. So if we go again we have sorted out which room we would stay in for minimal steps. The staff couldn't be more helpful. The building is built into a hillside, its old and very pretty. The location is amazing."

Stone House Hotel

10/10 Excellent

"Lovely hotel. Beautiful setting with an amazing view. The reviews we read before we stayed, said the staff were wonderful and friendly. Reviews often say this about hotels and we were just expecting the usual professional staff. However it must be said the staff were superb, stood out and had a major positive impact on our stay making it so enjoyable. The evening dinner very good. The breakfasts excellent. Definitely a place to stay."

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winton vacation rentals we have selected for you start as low as CA $308 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 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?

Oughtershaw Hall - a large propertie that sleeps 16 guests in 8 bedrooms: Visitors like this Winton vacation home rental. It is located in a rural location and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher to make your meal-planning easier. It offers a patio, a garden, and an arcade game room so you can immerse yourself in your vacation.

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 Appleby Castle 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.

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Check prices for these dates

Our top choices for Winton vacation rentals

1. Muddy Boots – Scarpa.

2. Muddy Boots - Arcade Royale

3. Cosy Nook Cottage

4. The Elm Shepod - Smardale Mill - Modern cosy glamping pod with amazing views, Sleeps 4 guests in 1 b

5. Cherry Tree Cottage

6. The Ash Shepod - Smardale Mill - Fabulous glamping pod/shepherds hut, sleeps 4 guests in 1 room

7. A spacious detached cottage located by a beck in a quiet village.

8. 3 bedroom accommodation in Newbiggin on Lune, near Kirkby Stephen

9. Curlew Lodge - sleeps 6 guests in 3 bedrooms

10. Cosy 2 bed-room cottage near High Force Waterfall

11. 1 bedroom accommodation in Appleby-in-Westmorland

12. Howgills Apartment 7 (self-catering accommodation with free parking and Wi-Fi)

13. 2 bedroom accommodation in Barnard Castle

14. Studio flat, views of Whernside , perfect base for exploring the Yorkshire dales

15. Burn Bank

16. A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.

17. High-quality bolthole and cosy sanctuary for 2 people in a picturesque village location with WiFi.

18. River Dance Cottage

19. Howgills Apartment 11 (self-catering accommodation with free parking and Wi-Fi)

20. The Yorkshire Dales Snug - Walkers' Delight - Pet Friendly

Find vacation rentals that suit your style

Top Winton Hotel Reviews

Shap Wells Hotel

Westmorland Hotel Tebay

The Charles Bathurst Inn

The Fox Hall Inn

Stone House Hotel

Tufton Arms Hotel

Appleby Castle

Haweswater Hotel

The World Famous Tan Hill Inn

Find out more about Winton

Frequently asked questions

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