Middleham Vacation Rentals from CA $585: Short-Term Rentals for 2026

Q: What's the top vacation rental in Middleham?

Hill Top Farm, Askrigg, Yorkshire Dales : This vacation home near Middleham offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. You and your friends and family can relax into your vacation with amenities like an arcade game room.

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Our top choices for Middleham vacation rentals

A stone building with a round shape, a wooden door, and a small window. There is a table and chairs outside, surrounded by plants and flowers.

1. The Round House

Leyburn

CA $681 total

includes taxes & fees

Oct 22 - Oct 23

A hotel room with a neatly made bed, two pillows, a bedside lamp, and a window with curtains.

2. Cosy cottage in the heart of Middleham famous for its horse racing stables.

Middleham, near Leyburn

Paul Tasker

CA $752 total

includes taxes & fees

Oct 30 - Oct 31

A bedroom with a bed, bedside tables, a dresser, a mirror, and a chair.

3. Prospect House

Leyburn

ANTHONY

CA $843 total

includes taxes & fees

Oct 8 - Oct 9

A modern kitchen with white cabinets, a wooden countertop, and a built-in oven. There is a dining area with white chairs and a table set for two.

4. White Swan Cottage

Leyburn

"This is a beautifully appointed cottage with everything you need for a comfortable stay. It's in a quiet location looking out onto a courtyard. Although there is no onsite parking, we had no trouble finding a parking space on the square. Visitors should also be aware that there is no outdoor seating area but we were out and about so this wasn't a problem for us. We would recommend the fish and chip place - but go for small fish and chips! The large are for those with a very large appetite! ...

Janet

CA $861 total

includes taxes & fees

Oct 8 - Oct 9

5. Kelda Garthr

Leyburn

CA $822 total

includes taxes & fees

Oct 31 - Nov 1

A courtyard with a table set for tea, a chair, and potted plants.

6. Demonicus

Leyburn

CA $1,068 total

includes taxes & fees

Oct 8 - Oct 9

A stone building with a green door, a window with a white frame, and a table with chairs outside.

7. Teal Cottage

Leyburn

CA $681 total

includes taxes & fees

Oct 17 - Oct 18

A bedroom with a bed, a wooden dresser, a chair, a mirror, and a shower area.

8. In & Out Cottage

Leyburn

CA $637 total

includes taxes & fees

Oct 10 - Oct 11

A stone building with a patio area featuring a table and chairs.

9. Beningborough

Leyburn

CA $2,123 total

includes taxes & fees

Oct 8 - Oct 9

A stone building with multiple windows, a door, and a small garden with flowers and a hedge.

10. Cartmel Cottage

Leyburn

CA $577 total

includes taxes & fees

Oct 23 - Oct 24

A window with a clear view of a rural landscape, including barns and a grassy field.

11. 1 bedroom accommodation in East Witton, near Leyburn

East Witton, near Leyburn

Paul Roney

CA $579 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a washing machine, oven, and a view of the outside.

12. 66 Dale Grove

Leyburn

Nicola

CA $649 total

includes taxes & fees

Oct 13 - Oct 14

A wooden shelf with decorative items and books.

13. The Den - Small but cosy apartment in the Dales.

Leyburn

JOANNE

CA $147 total

includes taxes & fees

Oct 5 - Oct 6

A neatly made bed with a striped bedspread, a bedside table with a lamp, and two framed botanical prints on the wall.

14. The Drey Apartment - self-catered Dales luxury

Leyburn

Kevin

CA $189 total

includes taxes & fees

Oct 6 - Oct 7

A cozy cabin interior with a wooden ceiling, a purple sofa, a TV, a fireplace, and a dining area with a table and chairs.

15. 2 bedroom accommodation in Charlcot, near Masham

Charlcot, near Masham

Richard Johnson

CA $521 total

includes taxes & fees

Oct 12 - Oct 13

A cozy living room with a fireplace, a wooden ceiling, and a large window.

16. 17th-century cottage overlooking village green.

Crakehall

Julie C.

CA $650 total

includes taxes & fees

Oct 23 - Oct 24

A dining area with a wooden table and chairs, a vase, and a cabinet with glass doors.

17. 5 bedroom accommodation in Hudswell, near Richmond

Hudswell, near Richmond

Mark Hawkins

CA $854 total

includes taxes & fees

Oct 14 - Oct 15

A stone building with a well-maintained garden, including a circular lawn and various plants.

18. Dog Friendly Cottage with Private Drive, Enclosed Garden, Central Heating, Free WiFi & pubs nearby

Richmond

Paul S.

CA $958 total

includes taxes & fees

Oct 12 - Oct 13

A kitchen with white cabinets, a wooden countertop, a microwave, a sink, a stove, and a fruit bowl.

19. Morton House & The Stable Block, Grade 2 listed farmhouse in the heart of Masham

Masham

Anonymous traveller

CA $1,085 total

includes taxes & fees

Oct 5 - Oct 6

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

20. River Dance Cottage

Leyburn

Adam

CA $444 total

includes taxes & fees

Oct 5 - Oct 6

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Top Middleham Hotel Reviews

The Wensleydale Hotel

10/10 Excellent

"Nice and pleasant hotel room well kept and the staff was excellent breakfast was great plenty off drinks to chose from highly recommend"

The George Of Piercebridge

8/10 Good

"This is an old coaching inn with a lot of history and the location can’t be faulted. I did feel that the exterior and interior of the building need investment and could do with a refurb. The staff make every effort and work very hard. They are all helpful. The bar was cosy and we liked the bar dining room for dinner. My only suggestion is to not use the deep fat fryer for Yorkshire puddings. Finally we had read great reviews about breakfast but were very disappointed; to coffee was much too weak and the English breakfast was very low grade with eggs fried in a lot of oil and a poor quality sausage."

The Green Dragon Inn - Hardraw

8/10 Good

"If you're a all creatures great and small fan, it's perfect, as you walk in you actually walk into the "drovers". If you're not a fan it will take you back it's an unchanged farmers country pub, but don't let that deter you, the rooms are stunningly clean, the staff friendly and very attentive."

The Kings Head Hotel, Richmond, North Yorkshire

8/10 Good

"The hotel reception, outside area, bar and restaurant were all great. The room was clean, the bathroom had been updated and was fine. The windows needed drastic attention, we could not move them due to the state of repair, I assume there is some sort on 'listed building status' but they really need attention. The location and everything else was great."

Kings Head Masham by Chef and Brewer Collection

8/10 Good

"My wife and I were pleasantly surprised just how nice the hotel was, the staff were really nice and the room very comfortable and cleaned daily, it's an old building so it's not like a modern hotel but adds to the character with oak beams, the only downside was no lift so as we were on the top floor it was a bit of a haul with the suitcases but the view of the market square was quaint. However the breakfast is amazing, choice of cerials, juices, milks, tea, coffee, pastries, muffins, breads butters, jams and a toaster plus an extensive cooked breakfast menu or they will cook you any combination The village of Masham is small but well situated to travel around Yorkshire. We loved every day and visited Harrogate one day which has a lovely park"

Find out more about Middleham

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

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Middleham. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Middleham?

Yes, we offer vacation rentals close to popular local attractions in Middleham, or you can choose a more remote option if you're looking for a relaxing stay. Middleham is known for its bars.

What's the top vacation rental in Middleham?

Hill Top Farm, Askrigg, Yorkshire Dales: This vacation home near Middleham offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. You and your friends and family can relax into your vacation with amenities like an arcade game room.

How many vacation rentals will I find in Middleham?

Choose from 11 Expedia vacation rentals in Middleham for a memorable vacation.

What can I see and do in Middleham?

Explore the area and family-friendly sights such as The Forbidden Corner, or get out into nature at a spot like Yorkshire Dales National Park. In the larger area, you’ll find Middleham Castle and Jervaulx Abbey.

What are vacation rentals like in Middleham?

Vacation rentals are private properties you can stay in for a couple days or more in Middleham. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you a great travel experience. 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 choice for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Middleham vacation rentals

1. The Round House

2. Cosy cottage in the heart of Middleham famous for its horse racing stables.

3. Prospect House

4. White Swan Cottage

5. Kelda Garthr

6. Demonicus

7. Teal Cottage

8. In & Out Cottage

9. Beningborough

10. Cartmel Cottage

11. 1 bedroom accommodation in East Witton, near Leyburn

12. 66 Dale Grove

13. The Den - Small but cosy apartment in the Dales.

14. The Drey Apartment - self-catered Dales luxury

15. 2 bedroom accommodation in Charlcot, near Masham

16. 17th-century cottage overlooking village green.

17. 5 bedroom accommodation in Hudswell, near Richmond

18. Dog Friendly Cottage with Private Drive, Enclosed Garden, Central Heating, Free WiFi & pubs nearby

19. Morton House & The Stable Block, Grade 2 listed farmhouse in the heart of Masham

20. River Dance Cottage

Find vacation rentals that suit your style

Top Middleham Hotel Reviews

The Wensleydale Hotel

The Golden Fleece Hotel, Thirsk, North Yorkshire

The George Of Piercebridge

The Green Dragon Inn - Hardraw

Blackwell Grange Hotel

The Kings Head Hotel, Richmond, North Yorkshire

Hotel Bannatyne Darlington

Holiday Inn Darlington - A1 Scotch Corner by IHG

Kings Head Masham by Chef and Brewer Collection

Find out more about Middleham

Frequently asked questions

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