Secure your stay for £20 T&Cs apply

Middleham Cottages

148 properties found

An outdoor area with stone walls and furniture at Poppy's Footprint in Leyburn

Poppy's Footprint

Middleham. Wensleydale, Yorkshire Dales - South

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£389

An outdoor patio with wooden table and chairs in front of a round stone building with a wooden door and small windows at The Round House in Middleham Wensleydale

The Round House

Middleham, Wensleydale, Yorkshire Dales - North

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£387

A cabin with a deck and grassy area at Badgers Retreat - Two Dales Richmond

15 Badgers Retreat - Two Dales

Tunstall, North Yorkshire, Yorkshire Dales - North

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£611

A stone house with a dark roof and two arched windows a tree in front and a stone pathway on a grassy lawn at Woodland View in Richmond

Woodland View

Richmond, Yorkshire Dales - North

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£601

A stone house with windows and wooden doors surrounded by greenery and a garden at The Summer Palace in Middleham Wensleydale

The Summer Palace

Middleham, Wensleydale, Yorkshire Dales - North

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£387

An outdoor area with a table and chairs at Olive Cottage in Richmond

Olive Cottage

Richmond, Yorkshire Dales - North

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£369

Stone building with green doors and windows with grass and bushes in front at Prospect Barn in West Witton

Prospect Barn

West Witton, Yorkshire Dales - North

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£447

Stone cottage with white windows and doors and a small garden with flowers and outdoor furniture at Cartmel Cottage in Middleham

Cartmel Cottage

Middleham, Yorkshire Dales - South

3 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£349

An outdoor area with a lodge and a surrounding fence at 10 Poppy Lodge in Richmond
New

10 Poppy Lodge

Catterick, North Yorkshire, Vale of York & Yorkshire Wolds

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£471

Stone exterior of a two story house with white door and window with bushes near the entrance at Kelda Garthr Tranquil Garden in Middleham

Kelda Garthr (Tranquil Garden)

Middleham, Yorkshire Dales - South

5 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£450

A stone house with a bay window and a garage with a green door at 10 Old School Close in West Witton

10 Old School Close

West Witton, Yorkshire Dales - South

3 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£420

A stone exterior of a residential building with two white front doors and several windows with a small garden in front at 66 Dale Grove Leyburn

66 Dale Grove

Leyburn, Yorkshire Dales - North

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£362

A garden with stone walls and a green door at Wedgewood Cottage in Middleham

Wedgewood Cottage

Middleham, Yorkshire Dales - North

3 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£454

A row of cottage front doors with potted plants on a cobbled street at Demonicus in Middleham

Demonicus

Middleham, Yorkshire Dales - South

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£520

An outdoor patio area with two cushioned wicker chairs stone walls and a wooden building at The Dove Cote in Brompton-on-Swale

The Dove Cote

Brompton-on-Swale, Yorkshire Dales - South

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£515

A stone house with windows and a door in a residential area at Eastend Cottage
Offer

Eastend Cottage

West Witton, Yorkshire Dales - North

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£539

A living room with a sofa and television at Askrigg in Aysgarth

Askrigg

Aysgarth, North York Moors & Coast

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£610

Exterior entrance of a stone and cream building with a white door a bench and potted plants at Daisy Cottage in Leyburn

Daisy Cottage

Leyburn, Yorkshire Dales - South

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£514

A cabin with a deck and steps at The Falls (Pet) Leyburn

The Falls (Pet)

Aysgarth, North York Moors & Coast

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£690

A stone and brick exterior wall with a blue door and window at The Hayloft in Brompton-By-Swale

The Hayloft

Brompton-By-Swale, Yorkshire Dales - North

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£366

If you are looking for a fascinating stay in a historical centre, look no further than a selection of holiday cottages to rent in Middleham. The small market town was once regarded as the 'Windsor of the North' due to its royal heritage, boasting a twelfth century castle that was once the childhood home of the infamous King Richard III, which also possesses the North of England's largest castle keep.

Discover Middleham's long-standing equestrian history

Explore the market town's quaint, winding streets, wander through the cobbled market squares all the while admiring the beautiful Georgian and Victorian architecture. The sport of Horse racing has long been linked to the town of Middleham. It was in 1773 that the first documented reference involving racehorses at Middleham was recorded, in the years since it has become synonymous with breeding and training racehorses and is still seen as one of the top training centres in the UK.

For 360-degree views across the Yorkshire Dales, climb up to the remains of Middleham Castle, a splendid medieval keep and once home of Richard III. Equally splendid is the outlook from Leyburn Shawl, a stunning limestone escarpment that was the escape route of Mary Queen of Scots as she fled from Bolton Castle - another medieval fortress not to miss.

Take a tour around the famous training centre or visit some of the charming town's art galleries, tearooms and pubs. Other nearby attractions include real ale breweries, historic sites like Jervaulx Abbey, the gardens of Constable Burton Hall, not to mention the spectacular waterfalls of Aysgarth and West Burton. You can also venture to the nearby towns of Northallerton and Ripon.

Whatever your tastes and hobbies, you will find plenty of things to do on a holiday in Middleham. If you still haven't found your perfect cottage, check out these dog-friendly cottages in the Yorkshire Dales.

Manage Your Cookie Preferences

We use cookies to enhance your browsing experience, analyse our traffic, personalise content and for marketing purposes including the personalisation of ads on the internet. We also set cookies that are necessary for our website to work. You can accept, decline, or manage your cookie preferences by clicking the appropriate button. More information about Google ads can be found in our cookie policy.