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Osmotherley, North Yorkshire
Sleeps 4
Bedrooms 2
Bathrooms 2
Change Fri
No Dogs
5 star
Enclosed garden / patio
Open fire / woodburner
Internet access
Pub nearby
Shop nearby
Family friendly
Towels included
Travel cot available
Highchair available
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At a glance

  • Beautiful 17th century cottage sleeping four people
  • Ideal for a getaway with friends or a family holiday
  • Modern comforts and traditional themes, with original period features
  • Toasty wood burner for chilly winter evenings
  • Perched on the edge of the dramatic North York Moors
  • Encompassed by heather-clad hills home to countless country walks
Property code: G0030

Once a drover's inn, this property has embraced its latest chapter in style. Elegant, spacious and inviting, the interiors demand rest and relaxation, whilst outside wild beauty and adventure calls.

A stunning two-bedroom stone cottage nestled on the cusp of the North York Moors, the building dates back over 400 years. This beautiful and historic property has been completely refurbished to offer the very best in self-catering accommodation. And surrounding you on all sides are heather-clad hills and breathtaking Yorkshire countryside - just heavenly!

In a former life, this accommodation was once a drovers' inn; the wide stretches of turf here provided a good overnight stopping place or 'stance' for the drovers' cattle on their way down from Scotland. The history and character of the building remain in abundance, with all of today's modern comforts thrown in.

Step inside to discover a handsome reception hallway with Yorkshire flagstones underfoot. Plenty of space to hang up coats and store muddy walking boots after a hike across the moors. With a cosy sofa and easy chair by the window it's a nice spot to snuggle away for the afternoon with a good book.

To the left of the entrance hall is the generous kitchen / diner which boasts uninterrupted views from every window. The gorgeous kitchen features dark grey units, solid oak work-tops, and a Belfast sink. The natural spring water running through the taps is a nice surprise. You'll find all mod cons in here including an induction hob, dishwasher, fridge, freezer and a range cooker. There's also a coffee machine for that morning cuppa and a gas stove in the inglenook fireplace keeps everything nice and toasty. There's a dining table set in the kitchen, perfect for those lazy holiday breakfasts where you can take your time over the morning papers. And for those more formal evening meals, there's a further beautiful dining area within the main living area.

This area is also home to the lounge where the star of the show is a gorgeous wood and brick inglenook fireplace. Complete with a large wood-burning stove this really feels like the heart of the home, where you can settle down for the evening by the glow of a real fire. Catch up over a glass or two of wine or enjoy a movie night on the TV.

Both bedrooms are on the first floor and feature luxurious king-size sleigh beds. Both rooms also enjoy en-suite shower rooms with top quality Stoves sanitary wear and complimentary Temple Spa toiletries. The perfect rooms to retreat to after a long day's sight-seeing. And the views when you wake each morning are the ultimate inspiration for the next day's adventures. Outside you'll find a very pleasant gravelled seating area which takes full advantage of the stunning scenery. Settle down to lunch here during the summer months or enjoy an atmospheric sundowner as the heather lights up in the evening sun. An old chequers board on the wall of the cottage reminds you of the history and character of this wonderful Yorkshire cottage.


  • 2 bedrooms: 2 king-size sleigh beds
  • 2 bathrooms: 2 en-suite shower rooms
  • Regret no pets
  • Range cooker and hob, dishwasher, fridge/freezer, coffee machine
  • Gas stove
  • Wood burner (first basket of logs included)
  • Smart TV
  • Wi-Fi included
  • Gravelled area outside
  • Off-road parking for 4 cars
  • Pub within 1 mile
  • Shop within 1 mile

High up in a beautiful spot in the western reaches of the North York Moors, designated an Area of Outstanding Natural Beauty in 1987, the property enjoys close proximity to the lush pastures and woodlands. The western Moors play host to grand country houses, atmospheric ruins and handsome market town and the views from here are simply stunning, and there are walks and cycle routes in every direction. You very close to the famous Cleveland Way as well as many more well-known and picturesque moorland walks, some of which lead all the way to the sea.

Although the cottage has a magnificent and uninterrupted position in the moors, it is also just a few miles from the vibrant little village of Osmotherley. Well known as a starting point for walkers and cyclists, this gorgeous little place is real picture-postcard stuff. It also offers excellent facilities including a cafe, village stores and a fish 'n chip shop. If you're a bit of a foodie, this part of Yorkshire is packed with fantastic gastro-pubs, restaurants and delis. The beautiful market town of Helmsley is within easy driving distance and is well worth a visit. If you fancy a little pampering you'll find the Verbena Spa here; perfect for a little me time indulgence.


This property is personally managed by Phil.

Guest comments

Reviewed by Hilary

10/10. Highly recommended! Beautiful Cottage. Luxurious interior. Great host/owner. Fabulous situation.

Reviewed by Stefanie 2nd March 2019

Wonderful cottage in a gorgeous location- would definitely recommend!

Reviewed by Gillian 11th February 2019

Lovely cottage, fantastic views and the owner Emma is brilliant.

Reviewed by Tracy 29th January 2019

Lovely cottage with fabulous views. Great for a peaceful weekend and some walking.

Reviewed by Janette 8th December 2018

Beautiful cottage lovely and warm and the host is excellent few minor details no scissors no pan lids no large pan as we like to cook it made it hard work and we wiped the lights above table in kitchen as really dusty as where other places other than that had a good holiday

Reviewed by Elaine 17th November 2018

Emma has put loads of effort into Chequers, ensuring it is comfortable and charming. She has thought of everything. Would recommend the cottage.

Reviewed by Anne 27th October 2018

Lovely cottage, has everything you need, nice little touches with the hamper and fresh flowers, amazing views.Would highly recommend!

Reviewed by Julie 6th October 2018

Lovely accommodation in a lovely setting, giving the feeling of being away from everything, yet within easy reach to the village of Osmotherley below. The accommodation is beautifully furnished by Emma (who needs to venture into interior design) as well as being very comfortable. A treat to come back to after visiting the surrounding area.

Reviewed by Kathy 5th October 2018

Amazing place, beautiful cottage and location, couldn't fault it

Reviewed by Stephen 12th August 2018

We had a lovely time in the beautiful Chequers cottage, and will definitely book again.

Reviewed by sheila 3rd July 2018

The cottage was very homely and had high standards of furniture. The cottage was very clean. The bed was very comfortable. There were lovely views over the moors. Emma, the welcome basket of goodies was a lovely bonus. You made us feel very welcomed. thank you.

Reviewed by Valerie 16th June 2018

We had a lovely two week stay at Chequers. The location was great for us as we are keen walkers and there were plenty of walks from the cottage. Chequers was very well equipped and the bed super comfy, all in all a super place to stay.

Reviewed by Jon 30th May 2018

A really gorgeous cottage. Emma, our host, was delightful and the attention to detail was superb. She has spoiled us for further renting - it is unlikely that anywhere else will meet the same standard

Reviewed by Lorna 7th May 2018

One of the best cottages we have rented over a number of years.

Reviewed by Jenny 28th April 2018

Chequers is a fabulous cottage in a spectacular location, we struggled to drag ourselves away! However, with some great walks from the doorstep and superb pubs, restaurants and places of interest just a short drive away, you knew that this beautiful retreat with it's amazing views, would greet you on your return. Emma, with her warm welcome has cRead morereated this gorgeous home with much love - we look forward to seeing you again soon! X Hide

Reviewed by Angela 25th April 2018

Feeling so reluctant to share this review as we'd like to keep The Chequers under wraps. It's fantastic. We've stayed at lots of cottages over many years and this is one of the rare occasions we've felt immediately relaxed. So often with these holiday cottages it's felt that the cost didn't quite balance with the experience but they definitely haveRead more this priced at the right level.The welcome was great too... not just a 'the keys are under the mat' kind of arrival, this was an actual introduction to the cottage. If only all hosts were as kind and thoughtful as Emma. She thinks about the little touches that really do, for those that notice, make all the difference. She's responsive and available all the time and I don't think anything would be too much trouble. We'd like to return again with the children but would also go on our own for lots of challenging bike rides and meandering walks. We did lots of walks in the area but you do need a car to get provisions. As for eating out, The Three Tuns is a great place to go in the village for good food and friendly service. We would have booked for Christmas but sadly, someone beat us to it.The wifi isn't fast and therefore netflix didn't work particularly well but we really didn't care. A superstar gem of a hideaway. Hide

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Note: As the postcode is used to identify the general area of the property, it may not always reflect its precise location, therefore please only use this map as a guide.

With a varied landscape of windswept dales, heather-clad moors and dramatic coast, interspersed with picturesque towns and villages, vibrant cities and a rich historical heritage, Yorkshire is rightly considered one of Britain's premier holiday destinations. Known as 'God's Own County', Yorkshire has nearly one-third of England's National Parkland, two Areas of Outstanding Natural Beauty and three sections of coastline designated as Heritage Coast.

Offering infinite opportunities for lovers of the great outdoors, the wild expanse of the Yorkshire Dales National Park in North and West Yorkshire is a glorious mix of awe-inspiring scenery, imposing castles, characterful Dales' villages and drystone walls. While to the east, the North York Moors National Park offers atmospheric moorland, fragrant pine forests and charming towns tucked away within steep-sloped valleys. Extending all the way to the Yorkshire Coast, you can even experience a traditional day at the seaside at popular resorts including Whitby, Flamborough and Scarborough. It's a beautiful terrain to explore.

A visit to the historical city of York is a must. Renowned for its medieval architecture, the magnificent York Minster and a myriad of museums, independent shops and exceptional eateries, you will not be disappointed. Then there's the chalk landscape of the Yorkshire Wolds, known to have inspired David Hockney. And with a packed calendar of events and festivals each year, including the Malton Food Festival, the Tour de Yorkshire and the Great Yorkshire Show, there's always something exciting to enjoy.

Our holiday cottages in Yorkshire are handpicked to ensure a luxurious and uniquely memorable experience. From dog-friendly cottages in the country to large family houses by the sea and romantic retreats in the city, we have a holiday in Yorkshire to suit everyone.

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