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


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

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.

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.

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Walking through the entrance hall into the kitchen you are once again greeted with spectacular views from every window. This beautiful country kitchen is spacious and roomy enough for a farmhouse table for relaxed suppers by the inglenook with its log stove. Everything you need has been thoughtfully provided by Emma, from the convenience of a dishwasher, induction hob, fridge, freezer and a range cooker to the expanse of units and generous oak work surfaces, 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 cooking up a treat a real pleasure.

Dining Room & Sitting Room

Wandering back through the hall into the generous sized formal dining room opening into the sitting room you are greeted with a magnificent inglenook and wood burner, there are sumptuous sofas and comfy armchairs to snuggle up and enjoy a night by the fire, there’s a TV for film nights and games and books for entertainment. Or just rest a while and enjoy those wonderful views with a glass of wine or two.


Climb the old wooden staircase to discover the two luxurious bedrooms on the first floor, the rooms have been elegantly appointed with king-size sleigh beds adorned with 1000 count Egyptian cotton inviting you to climb in and snuggle down. Both rooms are en-suite with top quality fittings, super soft towels and Temple Spa toiletries, 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.


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.


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.



2 spacious bedrooms with king size beds, both with views over the stunning moorlands


Both bedrooms have ensuite shower rooms


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.

On the map you can see the approximate location for the property.


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