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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.

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WiFi View from the front Rue Crofts View

Cropton - North York Moors

Rue Crofts View is a lovely two-bedroom cottage with great views over the North York Moors National Park within easy drive to Rosedale Abbey, Thornton le Dale and Dalby Forest.

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
£382 - £628 per week *

Y005 View property

  • Saturday changeover
  • 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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Pet Friendly 19 Burgate

Pickering - North York Moors

This beautiful listed stone built cottage is furnished and presented to a very high standard. It is spacious and well equipped and a perfect getaway for couples.

  • Friday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
£328 - £524 per week *

Y015 View property

  • Friday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 0.2 mile to a pub
  • 0.2 mile to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Freezer
  • No smoking
  • Welcome pack provided
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Pet Friendly The front entrance Stable Cottage

Cropton - North York Moors

Stable Cottage is a charming, pet friendly characterful cottage for couples surrounded by the beautiful countryside of the North York Moors. York, Pickering and Whitby are just an easy drive away.

  • Friday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets welcome
  • WiFi available
£328 - £524 per week *

Y030 View property

  • Friday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • On one level
  • 1 mile to a pub
  • 4 miles to a shop
  • Washing machine
  • Tumble dryer
  • No smoking

Pet Friendly Shared Swimming Pool Mallard Cottage

Newton On Rawcliffe - North York Moors

Full of character and charm, this property is comfortable and surrounded by open countryside. It has a ground floor bedroom and bathroom which are suitable for guests using wheelchairs. Pet friendly.

  • Saturday changeover
  • Sleeps 6
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets welcome
  • WiFi available
£430 - £983 per week *

Y256 View property

  • Saturday changeover
  • Sleeps 6
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets welcome
  • WiFi available
  • Open fire/woodburner
  • 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
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Special Offer Patio area Wayside Cottage

Wrelton - North York Moors

Wayside Cottage is a delightful, stone-built, well cared for cottage in the pretty village of Wrelton, just a few miles from the market town of Pickering and close to the North York Moors.

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
£364 - £597 per week *

Y195 View property

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels not provided
  • Barbecue
  • 0.5 mile to a pub
  • 2 miles to a shop
  • Washing machine
  • Travel cot available
  • Highchair
  • Stairgate
  • No smoking
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WiFi Entrance Hobbits Hideaway

Cropton - North York Moors

Hobbits Hideaway is a beautiful cottage offering high quality accommodation and situated in the charming village of Cropton near Pickering, on the border of the North York Moors National Park.

  • Saturday changeover
  • Sleeps 6
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
£401 - £658 per week *

Y004 View property

  • Saturday changeover
  • 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
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WiFi View from the garden Stable Cottage

Cropton - North York Moors

Stable Cottage offers high quality accommodation in picturesque surroundings, within easy drive to Pickering, Rosedale Abbey and Dalby Forest. It has a beautiful shared garden with large play area and private parking.

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
£364 - £597 per week *

Y006 View property

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

Middleton - North York Moors

Close to the market town of Pickering and the North York Moors, this is a high quality and well equipped eco-friendly Finnish log cabin, located in a quiet position.

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
£309 - £509 per week *

Y291 View property

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • On one level
  • 2 mile to a pub
  • 0.5 mile to a shop
  • Dishwasher
  • Freezer
  • Welcome pack provided

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Waterswallow Cottage near the charming village of Hutton Le Hole. Waterswallow Cottage

Hutton le Hole - North York Moors

A lovely 3 bedroom barn conversion in the North York Moors National Park, this is a great location for exploring North Yorkshire, walking, cycling, wildlife spotting, or just relaxing in stunning countryside.

  • Saturday changeover
  • Sleeps 4
  • 3 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Open fire/woodburner
£364 - £597 per week *

Y053A View property

  • Saturday changeover
  • 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

Pet Friendly Shared Swimming Pool Granary Cottage

Newton On Rawcliffe - North York Moors

On the same spacious site as the owner's house, in the centre of the popular but peaceful village of Newton on Rawcliffe

  • Saturday changeover
  • Sleeps 3
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
£295 - £533 per week *

Y258 View property

  • Saturday changeover
  • 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
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WiFi 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.

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
£459 - £580 per week *

Y034 View property

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Balcony
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 1.5 mile to a pub
  • 1.5 miles to a shop
  • Washing machine
  • Dishwasher
  • Freezer
  • No smoking
  • Welcome pack provided
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Pet Friendly Whistle Stop Cottage

Pickering - North York Moors

This charming property with an enclosed garden and private parking, situated on the outskirts of Pickering has been completely refurbished and offers pleasant and comfortable three-bedroom accommodation.

  • Saturday changeover
  • Sleeps 5
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets welcome
  • WiFi available
£346 - £567 per week *

Y035 View property

  • Saturday changeover
  • 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

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