Truly local, wherever you stay.

Good news! We’ve found 22 properties that match your search criteria You’re just a few clicks away from a holiday

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.

Exterior Fox Cub Cottage

Lockton - North York Moors

One of 3 ground floor cottages which can be booked together surrounded by purple moors. Enjoy the great outdoors with cycling ,walking and fishing on the doorstep. Then end the day with a meal at the local inn.

  • Sleeps 2
  • 1 Bedroom
  • Pet free property
£309 - £494 per week *

Y227 View property

  • Sleeps 2
  • 1 Bedroom
  • Pet free property
  • Towels not provided
Awarded 4 Star Gold with Original Cottages

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...

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Open fire/woodburner
  • Private parking
£439 - £692 per week *

Y012 View property

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4.5 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
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
£383 - £603 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

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
£308 - £483 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

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.

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
£326 - £513 per week *

Y291 View property

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Open fire/woodburner
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4.5 Stars
  • Towels provided
  • On one level
  • 2 mile to a pub
  • 0.5 mile to a shop
  • Dishwasher
  • Freezer
  • 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
£300 - £545 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 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
£401 - £628 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

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...

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet welcome
  • WiFi available
  • Private parking
£355 - £670 per week *

Y257 View property

  • 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

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.

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£401 - £634 per week *

Y045 View property

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
  • Bed linen provided
  • Garden/courtyard
  • 4.5 Stars
  • Towels provided
  • On one level
  • 0.3 mile to a pub
  • No smoking
  • Welcome pack provided

Exterior Little Fox Cottage

Lockton - North York Moors

Relax in the courtyard of this cosy cottage after a hard day exploring the Yorkshire coastline. Take a trip on the steam train through the Moors or hike through Dalby Forest and then enjoy a meal at the local inn.

  • Sleeps 2
  • 1 Bedroom
  • Pet free property
£309 - £494 per week *

Y228 View property

  • Sleeps 2
  • 1 Bedroom
  • Pet free property
  • Towels not provided
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
£364 - £573 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
Awarded 4 Stars with Original Cottages

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.

  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathroom
  • Pet free property
  • WiFi available
  • Private parking
£383 - £603 per week *

Y006 View property

  • 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

Loading properties 0

A maximum of 600 properties can display on the map. Please refine your search to reduce the number of properties, or go to list view to see them all.
Back to top

Looking for inspiration?

Places To See

View of Castle Howard in Yorkshire from the lake Yorkshire Revisited

I last went to Yorkshire as an undergraduate to study at the University of Leeds; this was in the days before students had cars, so opportunitie...

Read more