Middleham Cottages

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    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • Sleeps4
    • Bedrooms2
    • PetsNo

    A characterful cottage located in the village of Newbiggin in the Yorkshire Dales. Multi-fuel stove. WiFi. Ceiling beams. Charming location. Leyburn 7 miles; Hawes 9 miles. (Ref. 966542)

    7 nights from £346

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    • Barn Cottage - 966542 - photo 1
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    • Sleeps2
    • Bedrooms1
    • PetsYes

    A former garage converted to a lovely, romantic holiday home situated in the centre of Reeth in beautiful Swaledale. Cosy accommodation with WiFi. Woodburning stove. Outdoor seating with views towards Fremington Edge. (Ref. 14675)

    Last booked yesterday

    7 nights from £301

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    • Dibble Cottage - 14675 - photo 1
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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Charming, Grade II listed terraced cottage set around a pretty green in Richmond. Ideal base for friends and family in a peaceful setting. Courtyard patio, bike storage, very close to River Swale. (Ref. 954397)

    7 nights from £374

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    • 19 The Green - 954397 - photo 1
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    • Sleeps4
    • Bedrooms2
    • PetsYes

    A delightful semi-detached holiday cottage, a former cheese factory in the centre of Masham. Welcoming accommodation with a woodburning stove. Within easy reach of many attractions. Ripon 9 miles. (Ref. 904172)

    7 nights from £325

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    • Gromit Cottage - 904172 - photo 1
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    • Sleeps3
    • Bedrooms2
    • PetsYes

    A lovely cottage situated in the village of Grewelthorpe, North Yorkshire. Close to the pub. Near local woodland Hackfall woods. Pleasant views. Masham 3 miles; Ripon 6 miles. (Ref. 974792)

    7 nights from £307

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    • Lavender Cottage - 974792 - photo 1
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    • Sleeps4
    • Bedrooms2
    • PetsYes

    A charming cottage nestled in the village of Crakehall in the lower Yorkshire Dales. Smart TV. WiFi. Exposed beams. Bedale 2 miles; Leyburn 8 miles. (Ref. 971968)

    Last booked within the last 2 days

    7 nights from £303

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    • Edmunds Cottage - 971968 - photo 1
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    • Sleeps7
    • Bedrooms4
    • PetsYes

    A charming, detached cottage located in the village of Masham in North Yorkshire. Wood burner. Four bedrooms. Enclosed patio. Pet friendly. Ripon 9 miles; Bedale 6 miles. (Ref. 904411)

    7 nights from £421

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    • Wallace Cottage - 904411 - photo 1
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    • Sleeps4
    • Bedrooms2
    • PetsYes

    A charming stone cottage which sits in the village of Fearby in North Yorkshire. Nidderdale AONB. Pet-friendly. En-suite. WiFi. (Ref. 23683)

    7 nights from £352

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    • Bramblewick Cottage - 23683 - photo 1
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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Delightful studio apartment located in the centre of Richmond with castle views. Ideal for a romantic break. Great base for exploring Yorkshire Dales and North York Moors National Park. Barnard Castle 10 miles. (Ref. 917881)

    7 nights from £235

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    • Grace Cottage - 917881 - photo 1
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    • Sleeps4
    • Bedrooms3
    • PetsYes

    A stone-built period cottage just two minutes from the centre of Masham, cosy and warm with lots of character. Ripon 9 miles. (Ref. 904781)

    7 nights from £360

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    • Amberley Cottage - 904781 - photo 1
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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,