Chequers Cottage | Osmotherley | Beautiful Escapes
North York Moors National Park


  • 4
  • 2
  • 2
  • 1

Once a drovers’ inn, dating back over 400 years, Chequers was a regular stopover on the road down from Scotland where drovers would take an ale or two and rest their heads by the fire, while their cattle pastured on the moorland.

Today Chequers is a stunning old stone cottage and sits majestically in an unrivalled position overlooking sweeping moorland with its ever-changing colours. The rolling hills wrap around you and give you a great big Yorkshire hug as you watch the sheep grazing in the fields from every window, the views are truly magical. This is a very special place to BE.

From the moment you arrive at Chequers and meet Emma, the owner, who lives on the family farm next to the cottage you know you are in for a real treat. Emma has thought of everything you could possibly need and the little extras too that really make this cottage a beautiful escape.

You might have seen it featured in BBC Mortimer & Whitehouse: Gone Fishing Christmas Special! It really is a magical cottage for the festive season.

Children aged 10 years  and over and babes in arms are welcome.

Dog friendly.

If you have any questions about this property or any of our other properties choose how to contact us here.

Book with confidence, read our Covid 19 information

SHARE Chequers

Innkeeper's Cottage & Chequers Cottage

Innkeeper's Cottage & Chequers Cottage are separate cottages in the same location, they can be booked separately or together for up to 6 people. Perfect for a few friends or for extended family!


Living Space

The transformation of Chequers into a beautiful and luxurious cottage has been skilfully executed by Emma. Step inside this old stone cottage onto the Yorkshire flagstones and into the generous hall and take in the splendour of this magical place. The hall is spacious with a comfy old settle the perfect perch to pull off those hiking boots after a ramble across the moor, there’s a lovely armchair too, right by the window, just the spot for cosying up with a good book or whiling away the afternoon taking in the vista.

The main living space features carefully chosen furniture and fabrics that give the cottage a warm and luxurious feel, comfy sofas for relaxing and a magnificent fireplace with wood burner for chilly days, everything a country cottage should be with stone flagged floors, spectacular views across the Moor and lots of space for rest and relaxation, this is a beautiful cottage escape.

Kitchen & Dining

The pretty country kitchen is spacious and roomy enough for a farmhouse table for relaxed suppers, everything you need has been thoughtfully provided by Emma, from the convenience of a dishwasher, induction hob, fridge, freezer and a range cooker, there’s even a snazzy coffee machine that will satisfy the most discerning of coffee lovers.  All the essentials and some real luxuries that make holiday cooking a real pleasure.

There is a separate formal dining table in the main living space.


Climb the old wooden staircase to discover the first of the two luxurious bedrooms on the first floor. Moorland is an elegant bedroom with king-size sleigh bed adorned with 1000 count Egyptian cotton inviting you to climb in and snuggle down. En-suite with top quality fittings, super soft towels, the perfect combination for a bit of pampering. Emma has created a real sanctuary feel to the bedrooms and they too have spectacular views, imagine waking up to those wonderful views.


Also on the first floor, Heatherland is furnished and finished in a similar, elegant style with king sleigh bed, beautiful linens and a handy en-suite, and with breathtaking views across the moor what could be better than waking up to such a spectacular sight.

Terrace Garden

Venturing outside the cottage you’ll find a lovely seating area, the perfect spot to take in the stunning scenery, enjoy a spot of lunch or an early evening drink and watch the sunset over the moors as the changing light works its magic as it dances across the heather. This cottage has everything for the most beautiful escape imaginable, it will be difficult to steal yourself away from the enchantment of Chequers.


Chequer’s really is the best of both worlds, with the beautiful village of Osmotherley just a few miles away, here you will find the village stores, a café, gastro pubs and a fish and chip shop. The village is on the famous Cleveland Way and the starting point for the Lyke Wake Walk, making it a great meeting spot for groups of walkers and cyclists. Perfectly placed for exploring, from Chequers you can head west over to the Yorkshire Dales, go east to the coast or south to the historical City of York and if you decide to head North, the Cathedral City of Durham is a magical place to be.

Nearby Rievaulx Abbey, ree-VOH was a Cistercian abbey in Rievaulx, situated near Helmsley in the North York Moors National Park, North Yorkshire, England. It was one of the great abbeys in England until it was seized under Henry VIII of England in 1538 during the dissolution of the monasteries.

Also close by is the pretty village of Ampleforth where the Abbey has been home to a Community of Benedictine monks since 1802.The Abbey church is the centre of monastic life and everyone is welcome to join the Community for Mass and the Divine office. At other times the Abbey church is open to visitors who might like to simply look around. Explore the beautiful lakes, trails and woodlands or join a behind the scenes tour of the Abbey’s orchards and Cider Mill to see how Ampleforth Abbey’s famous cider and cider brandy is made.

The famous Castle Howard is just 30 miles from Chequers and well worth a visit. This magnificent house and gardens are simply breath taking, you may remember it from the Brideshead Revisited series which was filmed here. Evelyn Waugh’s stunning novel of duty and desire set amongst the decadent, faded glory of the English aristocracy in the run-up to the Second World War.

Good to know

Osmotherley Village with pubs and village store 1 mile

Supermarket delivery – Tesco


Washing machine

Garden Furniture

Coffee Machine




Logs included

Towels and linens included

Michelin Star restaurants – The Star at Harome & Black Swan at Oldstead




Chequers welcomes 1 small to medium dog no bigger than an average Labrador.

Dog bed provided.

Dog bowls provided.

Dogs are not allowed upstairs, there is a door to the staircase to help with this request.

Dogs are not allowed on the furniture.

Muddy/wet dogs must be cleaned off before entering the cottage.

Dog toileting must take place away from the cottage in the designated area and any mess cleaned up.

There may be a charge if additional cleaning is required.


Moorland Suite

King bed



Vanity Basin


King bed



Vanity Basin


Osmotherley & Helmsley

Perched up high on a beautiful spot on the West of the North York Moors Chequers sits in the heart of the rambling moor and rolling hills. Designated as an Area of Outstanding Natural Beauty the famous Cleveland Way is nearby and there is an abundance of walking trails and cycle routes quite literally on the doorstep, some of which take you east across the Moors to the sea.

Chequer’s really is the best of both worlds, with the beautiful village of Osmotherley just a few miles away, here you will find the village stores, a café, gastro pubs and a fish and chip shop. The village is on the famous Cleveland Way and the starting point for the Lyke Wake Walk, making it a great meeting spot for groups of walkers and cyclists.
As you amble around this picture postcard village with lots of history, discover the medieval church and the 18th century Methodist chapel, or follow the woodland path northwest of the village to the impressive ruins of Mount Grace Priory, the best-preserved Carthusian remains in the country.

Venture a little further to discover the beautiful picture postcard market town of Helmsley the only market town in the North York Moors National Park. It even has its own castle, a microbrewery, award winning shops and restaurants and the National Centre for Birds of Prey.

Osmotherley, Helmsley & local area

Discovering the wonderful local area is a highlight of any stay here. And the following attractions are all within easy reach of the apartments.

  • Osmotherley Village & Reservoir 1 mile
  • Helmsley – 16 miles
  • Northallerton – 7 miles
  • Thirsk – 12 miles
  • Ampleforth Abbey -20 miles
  • Sutton Bank visitor centre and cycle hire – 17 miles
  • City of York – 37 miles
  • Castle Howard – 34 miles
  • North Yorkshire Coast – 40 miles
  • Yorkshire Dales National Park – 31 miles


We love to hear back from our guests to find out their experience with Beautiful Escapes.

January 2022

We arrived at this beautiful cottage late afternoon on Monday 3rd January to be greeted by Emma. She was so welcoming.

The setting and location is outstanding with many walks to enjoy. We were lucky enough to wake up to snow the following morning and it just added to the atmosphere of the place. Our reason for coming was to celebrate our Golden Wedding and I can honestly say hand on heart there could not have been a better place to celebrate the occasion.

The kitchen is very well equipped, the rooms are spacious but full of cosiness. We both said we could quite happily move in and stay but home calls, so tomorrow the 7th, we leave.

Thank you Emma for putting so much love into Chequers, I am sure we will be back.

Thank you for the goodies,

Julie & Paul x

December 2021

Wonderful stay at Chequers, the cottage was a cosy sanctuary, beautiful walks, great pub in the village. Emma, the owner, made the stay extra special with her warmth. Thank You!

Paul & Julie

September 2021

Our break was much needed and the cottage provided us with all we needed for rest and relaxation. Lots to do in the local area so need to drive to far. Good food at both the Dog & Gun, Knayton and The Crathorne Arms. We were blessed with dry days and plenty of sunshine. Great to spend quality time with our dear friends of over 40 years.

Gary & Frances, Norfolk

May 2021

“What price charm” – from the moment we walked in we were completely in love with this charming, magical hideaway. Attention to detail, creative comfort together with atmospheric views, made for a lovely, delightful break.

Thank you Emma, we’ll be back – keep posting those photos!

A five star experience!

Richard & Sarah

April 2021

This is our second stay, we’ve had a lovely stay at Chequers cottage, exploiting the local walking, a trip to the coast and a visit to Helmsley. Loved ending the day with a drink on the terrace. We will return for our third stay!

Thanks for your hospitality, Dave & Zoe

April 2021

Thank you for an amazing stay at Chequers Cottage!

A fantastic cottage, a really lovely place, Emma & Andrew were so friendly and welcoming. We’ll definitely be back!

Really can’t recommend it highly enough! FAB!

Thanks, Julie, Lee, Sam & Little Meg x

A lovely week at Chequers whilst completing the Coast to Coast walk. Very spacious but cosy too & amazing views! Enjoyed our stay in a lovely part of the North York Moors.

Christine & Family, July 2020

We have returned to the very beautiful Chequers for the second time with an extremely warm welcome as always from Emma. A wonderful welcome hamper to greet us – Thank you so much, fresh flowers and a cosy, clean cottage. Our friends joined us for the first part of the week and they could not believe what a fabulous location and cottage it is. Thank you Emma for providing us with such a lovely base to explore the surrounding countryside, we have had an amazing week. Many, many thanks Lauren & Simon

Dear Emma Thank you for our beautiful stay in Chequers cottage, the flowers and welcome hamper were much appreciated as was your friendly and warm welcome. We could not have picked a better week with the glorious sunshine which realy showed off the wonderful views. We hope to return one day and would certainly recommend Chequers to friends and family. Many thanks, Kevin, Kare, Jordan & Nikita P.S. The fish & Chips were fab!

Fantastic week, amazing weather, cottage everything we could hope for, we will return! Many thanks, Ian & Vicky

A lovely relaxing break in a beautiful cottage in a stunning location. Thank you for the wonderful hamper and beautiful flowers on arrival. We look forward to coming again. Thank you for such a warm welcome, Emma, Ian & Sam