Middleham Cottages

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Your Middleham, North Yorkshire search returned 115 cottages

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  • Old Hall Byre

    Carlton-In-Coverdale, Yorkshire Dales - North
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    This delightful stone barn conversion resting in Carlton, near West Witton, North Yorkshire. Woodburning stove. Enclosed garden. Pet-friendly. Off-road parking. Middleham 4.6 miles; Leyburn 5.8 miles; Hawes 16.3 miles. (Ref. 1065459)

    7 nights from £587

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  • Castle View

    Richmond, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A welcoming Georgian townhouse in the centre of the market town of Richmond, North Yorkshire. Patio garden. Pet friendly. Amenities in walking distance. Close to Yorkshire Dales National Park. Leyburn 8.8 miles; Barnard Castle 14.3 miles. (Ref. 1051013)

    7 nights from £447

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  • Gromit Cottage

    Masham, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A delightful former cheese factory now semi-detached holiday cottage in the centre of Masham, North Yorkshire. Woodburning stove. Close to attractions. Off-road parking. Ripon 9 miles. (Ref. 1063816)

    7 nights from £409

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  • Daisy Cottage

    Leyburn, Yorkshire Dales - South
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    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)

    7 nights from £561

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  • 21 Millgate

    Richmond, Yorkshire Dales - North
    • Sleeps5
    • Bedrooms3
    • PetsYes
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    A wonderfully renovated end-terrace cottage resting in the heart of Richmond, North Yorkshire. Woodburning stove. Smart TV. Garden. Off-road parking. WiFi. Leyburn 9 miles; Barnard Castle 14.4 miles. (Ref. 1059883)

    7 nights from £450

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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 £475

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  • Woodland View

    Richmond, Yorkshire Dales - North
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    A contemporary first-floor apartment resting on the outskirts of Richmond in North Yorkshire. Open-plan. Private hot tub. Romantic. Darlington 14.6 miles; Northallerton 17.3 miles. (Ref. 1070889)

    7 nights from £576

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  • Wren Cottage

    Patrick Brompton near Bedale, North York Moors & Coast
    • Sleeps3
    • Bedrooms2
    • PetsYes
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    A quaint, detached cottage positioned in the rural village of Patrick Brompton near Bedale. Pet-friendly. Enclosed garden. Ideal for couples. Northallerton 11.6 miles; Darlington 19.4 miles. (Ref. 1067170)

    7 nights from £361

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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 £409

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  • 36 Badgers Retreat

    Tunstall near Catterick, North Yorkshire, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    A charming wooden lodge set on Badgers Retreat Holiday Park, North Yorkshire. All-ground-floor. Romantic Retreat. Countryside setting. Richmond 5.7 miles; Northallerton 14 miles; Ripon 22.1 miles. (Ref. 1061645)

    7 nights from £346

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  • 26 Bargate

    Richmond, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsNo
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    A quirky terraced cottage found in the vibrant market town of Richmond, North Yorkshire. Woodburning stove. Quirky. Castle views. Colburn 3.8 miles; Catterick 5.5 miles; Leyburn 8.8 miles. (Ref. 1050415)

    7 nights from £595

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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 £410

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  • Dibble Cottage

    Reeth, Yorkshire Dales - North
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    A former garage converted to a romantic, reverse-level holiday home in the centre of Reeth, Yorkshire Dales. WiFi. Woodburning stove. Outdoor seating with views towards Fremington Edge. Swale Dale 8.1 miles; Richmond 10.1 miles; Leyburn 10.3 miles. (Ref. 1062069)

    7 nights from £373

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  • Middle Cottage

    Middleham, Yorkshire Dales - South
    • Sleeps3
    • Bedrooms2
    • PetsYes
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    A delightful mid-terrace cottage with spacious accommodation. The cottage is a real delight with lots of character and contemporary styling. Great walks from the doorstep. Pets welcome. Leyburn 2.5 miles. (Ref. 929028)

    7 nights from £472

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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 £455

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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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  • Cleeve Cottage

    Middleham, Yorkshire Dales - North
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    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)

    7 nights from £422

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  • Fieldfare Lodge

    Middleham, Yorkshire Dales - South
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    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 £403

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  • The Coach House

    Middleham, Wensleydale, Yorkshire Dales - South
    • Sleeps8
    • Bedrooms3
    • PetsYes
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    Delightful, stone-built, semi-detached cottage in the town of Middleham, North Yorkshire. Oak beams. Roof terrace. Leyburn 2.5 miles. (Ref. 18757)

    7 nights from £826

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  • Kelda Garthr (Tranquil Garden)

    Middleham, Yorkshire Dales - South
    • Sleeps5
    • Bedrooms3
    • PetsNo
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    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)

    7 nights from £490

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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,