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Cottages in Middleton

A gateway to the natural beauty of Upper Teesdale and the Yorkshire Dales National Park, Middleton is at the heart of a stunning and hidden corner of England.

Beyond the town centre you will find areas of magnificent scenery in a landscape dominated by expansive wooded valleys, open moorland and picturesque villages. Hidden amongst these vales and hills lies High Force, England’s highest single drop waterfall, cascading 22m of unbroken water where the River Tees plunges over its dramatic precipice.

Wrapped by the North Pennines Area of Outstanding Natural Beauty (A.O.N.B) to the North, with the Yorkshire Dales to the South, Middleton is a quintessential Dales market town offering all your amenities as well as some fabulous eateries and watering holes. The area surrounding here and its nearest neighbour Barnard Castle has inspired poets and artists through the centuries, and a holiday here will allow you to follow in the footsteps of Turner, Dickens or Sir Walter Scott. Find inspiration from this wild and rich landscape and explore outstanding rock formations, waterfalls and native flora and fauna. The low-level light pollution in this area makes it perfect for stargazing, meaning you can get out and about day or night.

From converted barns to cosy stone cottages, many of our Middleton cottages welcome dogs, walkers and cyclists alike, making a stay here the perfect choice for any outdoor lover. If a stay in Middleton and the surrounding area sounds the perfect tonic for you and your loved ones, then search through the list of available cottages below and book an outdoor holiday. For more help and advice call our team on 0333 2020899.

Awarded 3 Stars with Original Cottages

Exterior view of Virginia Cottage in Thornton-le-Dale. Virginia Cottage

Thornton Le Dale - North York Moors

A stone cottage full of beams and stone floors with a large farmhouse kitchen and lovingly furnished throughout. Private gardens with a decking for alfresco dining and a hot tub to relax in after a hard day exploring.

  • Sleeps 5
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
£458 - £865 per week *

Y547 View property

  • Sleeps 5
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 3 Stars
  • Towels not provided
  • Hot tub
  • Washing machine
  • Tumble dryer
  • No smoking
Awarded 3 Stars with Original Cottages

Whistle Stop Cottage

Pickering - North York Moors

Charming, pet friendly property for five people with an enclosed garden in the North Yorkshire Moors

  • Sleeps 5
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
£337 - £651 per week *

Y035 View property

  • Sleeps 5
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 3 Stars
  • Towels not provided
  • 1 mile to a pub
  • 1 mile to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Freezer
  • Travel cot available
  • Highchair
  • Stairgate

Entrance Hobbits Hideaway

Cropton - North York Moors

Nestled on the edge of the North Yorkshire Moors National Park, this fantastic stone cottage is set on private land with a large garden and two other holiday cottages that can be hired for larger parties.

  • Sleeps 6
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£427 - £779 per week *

Y004 View property

  • Sleeps 6
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • Barbecue
  • 0.5 mile to a pub
  • 5 miles to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Freezer
  • No smoking
  • Welcome pack provided

Shared Swimming Pool Swift Cottage

Newton On Rawcliffe - North York Moors

A cosy cottage with stone walls and beams. Take a dip in the indoor swimming pool or relax in the sauna. Ride the North York Steam Railway into Heartbeat countryside or take a trip to Whitby or York.

  • Sleeps 5
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet welcome
  • WiFi available
  • Open fire/woodburner
£461 - £971 per week *

Y259 View property

  • Sleeps 5
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet welcome
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • Towels provided
  • Wet room
  • Hot tub
  • Swimming pool
  • On one level, no stairs
  • 0.2 mile to a pub
  • 4 miles to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Cot available
  • Highchair
  • No smoking
Awarded 4 Star Gold with Original Cottages

A beautiful cosy lounge with a warm log fire. Willowfield Cottage

Thornton Le Dale - North York Moors

Located in a quaint village on the North York Moors this luxurious three bedroom cottage, sleeping up to 5 people is perfect for walkers and cyclists. Dalby Forest and Flamingo Land theme park are also close by for famil...

  • Sleeps 5
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£443 - £841 per week *

Y057 View property

  • Sleeps 5
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4.5 Stars
  • Towels provided
  • Walk-in shower
  • Barbecue
  • 0.2 mile to a pub
  • 0.2 mile to a shop
  • Washing machine
  • Dishwasher
  • Freezer
  • Stairgate
  • No smoking
  • Welcome pack provided
Awarded 4 Stars with Original Cottages

Exterior - View 6 Forge Cottage

Thornton Le Dale - North York Moors

Located in the heart of a pretty village, this renovated 14th century old forge is a lovely holiday home for a family. Relax and listen to the stream that runs beside the cottage or explore the wonders of the village.

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Bed linen provided
£368 - £683 per week *

Y301 View property

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 0.3 mile to a pub
  • 0.1 mile to a shop
  • Washing machine
  • Tumble dryer
  • Travel cot available
  • No smoking
Awarded 4 Stars with Original Cottages

Woodpecker Cottage

Hutton le Hole - North York Moors

As the name suggests, the garden of this charming cottage is full of birds as is the surrounding woods. A real haven for nature enthusiasts with footpaths to several villages and close to the Yorkshire Wolds and Moors.

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • Private parking
  • Bed linen provided
£293 - £529 per week *

Y052A View property

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 1.5 mile to a pub
  • 2 miles to a shop
  • Washing machine
  • Tumble dryer
  • Travel cot available
  • Highchair
  • No smoking
Awarded 4 Star Gold with Original Cottages

There is a feature wall with exposed stonework. Morgan's Rest

Pickering - North York Moors

This beautiful, luxury one bedroomed cottage has been refurbished and presented to a very high standard. It is situated on the outskirts of the historic market town of Pickering.

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£519 - £683 per week *

Y034 View property

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Balcony
  • Garden/courtyard
  • 4.5 Stars
  • Towels provided
  • 1.5 mile to a pub
  • 1.5 miles to a shop
  • Washing machine
  • Dishwasher
  • Freezer
  • Travel cot available
  • Highchair
  • Stairgate
  • No smoking
  • Welcome pack provided

Shared Swimming Pool Granary Cottage

Newton On Rawcliffe - North York Moors

Why not take your horse on holiday with you ! This group of cottages provides DIY stabling. Set in large grounds with an indoor pool and surrounded by countryside and the Moors, it is also close to Skipton and Scarboroug...

  • Sleeps 3
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
  • Private parking
£331 - £591 per week *

Y258 View property

  • Sleeps 3
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • Towels provided
  • Hot tub
  • Swimming pool
  • 0.2 mile to a pub
  • 4 miles to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Cot available
  • Highchair
  • No smoking
Awarded 3 Stars with Original Cottages

Living area is all open plan. Birdie Cottage

Pickering - York & Vale of York

Situated on the outskirts of Pickering, Birdie Cottage is ideal for exploring Yorkshire Moors and Wolds. York, Whitby, Scarborough, Flamingo Land and Castle Howard are an easy drive away.

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets welcome
  • Private parking
  • Bed linen provided
£352 - £651 per week *

VY001 View property

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets welcome
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 3 Stars
  • Towels provided
  • On one level, no stairs
  • 0.1 mile to a pub
  • 1 mile to a shop
  • Washing machine
  • Freezer
  • Cot available
  • Highchair
  • No smoking
  • Welcome pack provided
Awarded 4 Stars with Original Cottages

Waterswallow Cottage

Hutton le Hole - North York Moors

A quaint cottage with stunning views and a garden where you can enjoy the evening bird song and try to spot a buzzard. Cyclists and walkers will be spoilt for choice with woods, trails and bridleways on the doorstep.

  • Sleeps 4
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Open fire/woodburner
  • Private parking
£352 - £651 per week *

Y053A View property

  • Sleeps 4
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 1.5 mile to a pub
  • 2 miles to a shop
  • Washing machine
  • Travel cot available
  • Highchair
  • No smoking
Awarded 4 Stars with Original Cottages

View from the front Rue Crofts View

Cropton - North York Moors

Set just four miles from the town of Pickering, made famous by its diverse market, this stunning stone cottage is ideally placed for enjoying the North Yorkshire Moors National Park.

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£397 - £683 per week *

Y005 View property

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • Barbecue
  • 0.5 mile to a pub
  • 4 miles to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Freezer
  • Cot available
  • No smoking
  • Welcome pack provided

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