Middleham Cottages

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  • Fieldfare Lodge

    Middleham, Yorkshire Dales - South
    • Sleeps2
    • Bedrooms1
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    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)

    7 nights from £339

    Secure this property with a 30% deposit* Book now
  • Wedgewood Cottage

    Middleham, Yorkshire Dales - South
    • Sleeps3
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    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)

    7 nights from £349

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  • Dillons Cottage

    Richmond, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A homely Grade II listed cottage in the centre of Richmond market town in North Yorkshire. Courtyard. Pet friendly. WiFi. Colburn 3.2 miles; Leyburn 8.5 miles; Darlington 12.6 miles. (Ref. 1054760)

    7 nights from £353

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    Last booked yesterday
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  • 6 Badgers Retreat

    Richmond, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A superb lodge with a hot tub property resting on the outskirts of Richmond. All-ground-floor. Pet-friendly. Barbecue. Barnard Castle 21.6 miles. (Ref. 1051715)

    7 nights from £427

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  • White Lea

    Reeth, Yorkshire Dales - North
    • Sleeps6
    • Bedrooms3
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    This stone-built cottage can be found in Grinton near Reeth, in the Yorkshire Dales National Park. Open-plan living. Woodburning stove and underfloor heating. Private enclosed patio with countryside views. Reeth 1.2 miles; Richmond 10 miles. (Ref. 1038538)

    7 nights from £409

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  • Jasmine Cottage

    Richmond, Yorkshire Dales - South
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A wonderful terraced property resting in Richmond, Yorkshire. Off-road parking. Electric fire. Pet-friendly. Barnard Castle 15.5 miles. (Ref. 1053052)

    7 nights from £320

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  • Honeysuckle Cottage

    Richmond, Yorkshire Dales - South
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A stone-built terraced cottage resting on the outskirts of Richmond. Pet-friendly. Off-road parking. Barnard Castle 15.5 miles. (Ref. 1053055)

    7 nights from £320

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  • Lavender Cottage

    Richmond, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    An end-terrace cottage resting on the outskirts of Richmond. Pet-friendly. River close by. Barnard Castle 15.5 miles. (Ref. 1051475)

    7 nights from £331

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  • The Summer Palace

    Middleham, Wensleydale, Yorkshire Dales - North
    • Sleeps2
    • Bedrooms1
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
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    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)

    7 nights from £343

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  • The Gatehouse

    Middleham, Wensleydale, Yorkshire Dales - South
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
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    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)

    7 nights from £453

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If you are looking for a fascinating stay in a historical centre, look no further than our 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 a 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,