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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 4 Star Gold with Original Cottages

WiFi Large driveway to the front of the property. Standfield Hall Cottage

Pickering - North York Moors

Placed in a tranquil countryside setting, this stone built cottage is just a short walk from the popular town of Pickering famous for its steam railway and market. Beautiful woodland walks are also easily accessible from...

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
£401 - £685 per week *

Y012 View property

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 1 mile to a pub
  • 1 mile to a shop
  • Washing machine
  • Tumble dryer
  • Dishwasher
  • Travel cot available
  • Highchair
  • No smoking
  • Welcome pack provided

Pet Friendly Shared Swimming Pool Owl Cottage

Newton On Rawcliffe - North York Moors

Part of a group of cottages, Owl cottage offers ground floor accommodation, set in lovely gardens. There is a shared indoor swimming pool with spa, sauna and also stabling for your own horse. Nearby is the North York Ste...

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
£350 - £655 per week *

Y257 View property

  • Saturday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • Towels provided
  • Hot tub
  • Swimming pool
  • On one level
  • 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

WiFi Rowan Lodge

Middleton - North York Moors

A Finnish log cabin with the eco credentials you would expect. Open plan, sylish and warm. Take breakfast on the decking overlooking the paddock before hiking along the many woodland trails for a spot of bird watching.

  • 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

Pet Friendly 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.

  • Saturday changeover
  • Sleeps 5
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet welcome
  • WiFi available
£405 - £900 per week *

Y259 View property

  • Saturday changeover
  • Sleeps 5
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet welcome
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • Towels provided
  • Hot tub
  • Swimming pool
  • On one level
  • 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

New Property Honey Pot Barn

Cropton - North York Moors

Beautiful, spacious one bedroom converted barn. This luxury property is full of character and charm with a wood burning stove and underfloor heating. Ideal for a romantic break.

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

Y045 View property

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • On one level
  • 0.3 mile to a pub
  • No smoking
  • Welcome pack provided
Awarded 4 Star Gold with Original Cottages

WiFi Silver Birch Lodge

Middleton - North York Moors

An eco-friendly Finnish log cabin close to the Yorkshire Moors. Open plan living area with a wood burner for cosy evenings and finished to a high standard throughout. Stabling available for your own horse. Enjoy spectacu...

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
£309 - £509 per week *

Y290 View property

  • Saturday changeover
  • Sleeps 2
  • 1 Bedroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4 Stars
  • Towels provided
  • 2 mile to a pub
  • 0.5 mile to a shop
  • Dishwasher
  • Freezer
  • No smoking
  • Welcome pack provided
Awarded 4 Stars with Original Cottages

Lounge has a high ceiling and exposed wooden beams. 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.

  • Friday changeover
  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • Private parking
£291 - £479 per week *

Y052A View property

  • Friday changeover
  • 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 Stars with Original Cottages

WiFi 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.

  • 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
Awarded 4 Stars with Original Cottages

WiFi View from the garden Stable Cottage

Cropton - North York Moors

Surrounded by large gardens and set close to the North Yorkshire Moors National Park, this classic country cottage is ideal for lovers of the outdoors. The interior has lots of character with many original features.

  • 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
Awarded 4 Star Gold with Original Cottages

Pet Friendly 19 Burgate

Pickering - North York Moors

Located close to Pickering Castle and many other interesting attractions, this marvellous old building is listed and kept to an immaculate standard. It is set in the ideal spot for exploring the Yorkshire coast and moors...

  • Friday changeover
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
£328 - £865 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
Awarded 4 Stars with Original Cottages

WiFi 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.

  • 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
Awarded 4 Stars with Original Cottages

WiFi Patio area Wayside Cottage

Wrelton - North York Moors

Spacious and comfortable stone cottage, close to the ancient market town of Pickering. A ride on the North York Moors railway is not to be missed and York, Whitby and Scarborough are all within an easy drive.

  • 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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