24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Middleham Cottages

REFINE SEARCH

Your Middleham, North Yorkshire search returned 128 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Stone-built, semi-detached cottage nestled in a quiet cul-de-sac, in the small village of West Witton. Off-road parking. Open fire. Yorkshire Dales National Park. (Ref. 989427)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from €520

Last booked 2 days ago
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A lovely stone annex cottage resting on the outskirts of Middleham, North Yorkshire. Woodburning stove. Romantic. Near to Yorkshire Dales National Park. Leyburn 1.3 miles; Richmond 10.5 miles. (Ref. 995948)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from €441

Last booked 6 hours ago
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Wensleydale cottage off market square in Middleham. Upside down accommodation. Woodburner, beams and stonework. Amenities on doorstep. Ideal romantic location. Leyburn 2.5 miles. (Ref. 972733)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from €441

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A perfect roundhouse cottage in a walled garden in the centre of Middleham, just perfect for a romantic trip! WiFi. Woodburner. Leyburn 2.2 miles. (Ref. 904812)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from €445

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A stone built mews cottage, resting in the town of Middleham, on the outskirts of the Yorkshire Dales National Park. Open fire. Enclosed garden. Close to amenities. Leyburn 2.4 miles; Richmond 11.7 miles. (Ref. 1024465)

  • Wi-fi
  • Dishwasher

7 nights from €438

Last booked yesterday
See more details
  • Sleeps7
  • Bedrooms4
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A traditional, three-storey terraced house situated in Leyburn, North Yorkshire. Enclosed garden. Close to amenities. Beautiful views. Richmond 9.4 miles. (Ref. 1084963)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €754

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A wonderful ground floor, detached cottage set in a walled garden just off the village square in Middleham, perfect for couples. En-suite bedroom. Woodburner. WiFi. Leyburn 2.2 miles. (Ref. 904813)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from €445

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A pretty, semi-detached bungalow sitting in Middleham in the Yorkshire Dales National Park, North Yorkshire. Close to amenities. Smart TV. Ground-floor living. Leyburn 2 miles; Richmond 11.7 miles. (Ref. 1077485)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • 10% off - Wed 13th Mar to 3rd Jun 2024

  • 10% off - Mon 3rd Jun to 28th Sep 2024

7 nights from €478

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful Grade II listed terraced cottage in the popular market town of Middleham. Set over three floors with original exposed beams and stonework, perfect for exploring the Yorkshire Dales. Leyburn 2.5 miles. (Ref. 943074)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from €508

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A pretty semi-detached cottage situated in Leyburn, North Yorkshire. Off-road parking. Enclosed garden. Woodburning stove. Close to amenities. Richmond 9.1 miles; Darlington 21.8 miles. (Ref. 1014717)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €659

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A charming, reverse-level barn conversion, set rurally in Ellingstring near Masham, North Yorkshire. Pet-friendly. Countryside views. In National Park. Romantic. Characterful. Bedale 9.7 miles; Ripon 14.3 miles; Northallerton 17.6 miles. (Ref. 1135711)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from €441

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely terraced cottage close to market square and amenities in Middleham. Cosy romantic retreat with beamed ceiling, open plan living area and cottage garden. Leyburn 2.5 miles. (Ref. 929525)

  • Wi-fi
  • Washing machine

7 nights from €439

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

An exquisite cottage nestled on the edge of the Yorkshire Dales National Park. Open-plan. Two woodburning stoves. Brilliant walking routes. Leyburn 2 miles. (Ref. 1012081)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €519

  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Fabulous 18th century, detached Leyburn cottage in a rural position in Yorkshire Dales National Park. Good family cottage with three bedrooms. Leyburn 4 miles. (Ref. 8082)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €581

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

This delightful stone cottage is located in Middleham, North Yorkshire. WiFi. multi-fuel stove. Enclosed patio area. Leyburn 2.5 miles; Richmond 12 miles. (Ref. 1001344)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from €531

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Charming, detached, stone cottage in idyllic location in Redmire. Cosy, characterful accommodation, beams, spiral staircase. Glorious riverside views. Close to steam railway. Leyburn 4 miles. (Ref. 29056)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from €479

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A charming, three-bedroom cottage resting in Redmire near Aysgarth, North Yorkshire. Pet-friendly. Countryside views. Original features. Near National Park. Woodburning stove. Family-friendly. Castle Bolton 1 mile; Leyburn 5 miles; Hawes 12.5 miles. (Ref. 1130141)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €728

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A contemporary link-detached cottage located on the outskirts of Middleham. WiFi. Multi-fuel stove. Off road parking. A great base for walking and exploring the old town, great gastropubs and lively local pubs abound. Leyburn 2 miles. (Ref. 916071)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from €574

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A smart cottage, a former gatehouse located on the market square at Middleham. En-suites, ground floor bedrooms, woodburner, WiFi. Leyburn 2.2 miles. (Ref. 905077)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from €660

  • Sleeps10
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Outstanding barn conversion on the outskirts of pretty Middleham. Beautiful long-distance views and just a short walk to the market square. Super king-size beds, en-suites, woodburner. Leyburn 2.2 miles. (Ref. 905078)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €1344

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.

Whatever your tastes and hobbies, you will find plenty of things to do on a holiday in Middleham. Book your self-catering accommodation today by calling one of our travel experts on 01244356666,