Having trouble logging in?

We’re currently experiencing a technical issue affecting customer account logins. Our IT team is on the case and working hard to fix it. There’s no need to contact us — your booking is completely safe, and you’ll be able to access your account again as soon as it’s resolved. Thanks so much for your patience!

Destinations and properties
Dates and flexibility
Select dates
Party makeup
Guests
Middleton • Dates • Guests
Middleton • Dates • Guests

Filters


Price range

Based on a 7 night stay

£370
£1,500+
Reset

Property makeup

Dogs allowed



Minimum star grading



Property type

Recently added

Middleton cottages

46 properties found
Pickering, Yorkshire

Rowan Lodge

211

Our grading

7 nights

£446 - £792

View
Pickering, Yorkshire

Silver Birch Lodge

2111

Our grading

7 nights

£446 - £792

View
Pickering, Yorkshire

Potter Hill Cottage

211

Our grading

7 nights

£491 - £797

View
Pickering, North Yorkshire

Isabella Cottage - Pickering

321

Our grading

7 nights

£583 - £901

View
Pickering, Yorkshire

Pantile Cottage

4212

Our grading

7 nights

£543 - £1,083

View
Middleton - North York Moors, Yorkshire

Coach House Cottage

4221

Our grading

7 nights

£744 - £1,361

View
Pickering, Yorkshire

Standfield Hall Cottage

421

Our grading

7 nights

£481 - £991

View
Middleton - North York Moors, Yorkshire

The Barn

532

Our grading

7 nights

£798 - £1,404

View
Pickering, Yorkshire

Whistle Stop Cottage

5312

Our grading

7 nights

£471 - £966

View
Pickering, Yorkshire

The Old Pottery - Pickering

8432

Our grading

7 nights

£1,319 - £1,319

View
Pickering, North Yorkshire

Railway Cottage - Pickering

1152

Our grading

7 nights

£1,219 - £1,950

View
These properties are nearby.
Normanby, North Yorkshire

Blacksmiths Cottage

2111

Our grading

7 nights

£729 - £1,126

View

Showing 1-12 of 46 properties

Holiday cottages in Middleton, Yorkshire

A gateway to the natural beauty of Upper Teesdale and the Yorkshire Dales National Park, Middleton near Pickering  and Thorton-le-Dale, 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 National Landscape 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.