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Middleham Cottages

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Your search returned 119 cottages.

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  • Demonicus

    Middleham, Yorkshire Dales - South
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A quaint mid-terrace cottage resting within the centre of Middleham. Close to all amenities. WiFi. Leyburn 2.1 miles; Richmond 11.3 miles. (Ref. 1060887)

    7 nights from £347

    Secure this property with a 30% deposit*
    Last booked 2 days ago
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  • Brookside Cottage

    Bellerby near Leyburn, Yorkshire Dales - South
    • Sleeps6
    • Bedrooms3
    • PetsNo
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    A charming property situated on the outskirts of Leyburn in North Yorkshire. Woodburning stove. Pet-friendly. WiFi. Off-road parking. Richmond 7.4 miles; Ripon 22.1 miles. (Ref. 1054837)

    7 nights from £423

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  • Pennycress Cottage

    Leyburn, Yorkshire Dales - South
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    A lovely stone-built terraced cottage in the market of Leyburn. Character and charm throughout. Romantic bolthole. Good touring base. Richmond 9.1 miles; Darlington 21.6 miles. (Ref. 1054524)

    7 nights from £348

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    Last booked yesterday
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  • Wedgewood Cottage

    Middleham, Yorkshire Dales - South
    • Sleeps3
    • Bedrooms2
    • PetsYes
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    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 £352

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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 £342

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  • 8 Badgers Retreat

    Tunstall near Catterick, North Yorkshire, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    This well-presented lodge rests in Tunstall near Catterick, North Yorkshire. All-ground-floor. Off-road parking. Rural location. Richmond 5.7 miles; Northallerton 14.4 miles; Harrogate 32.5 miles. (Ref. 1061010)

    7 nights from £554

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  • Honeysuckle Lodge

    Tunstall near Catterick, North Yorkshire, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A contemporary wooden lodge set on a wonderful complex within the village of Tunstall, North Yorkshire. Open-plan living. Electric fire. Private Veranda. Richmond 5.7 miles; Northallerton 13.8 miles; Darlington 16.2 miles. (Ref. 1060698)

    7 nights from £372

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  • The Round House

    Middleham, Wensleydale, Yorkshire Dales - North
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    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)

    7 nights from £342

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    Last booked yesterday
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  • Cartmel Cottage

    Middleham, Yorkshire Dales - South
    • Sleeps3
    • Bedrooms2
    • PetsYes
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    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)

    7 nights from £337

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  • In & Out Cottage

    Middleham, Wensleydale, Yorkshire Dales - South
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    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)

    7 nights from £386

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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,