Charming and cosy cottage for two offering a peaceful stay in a wonderful market town in Yorkshire.
Repurposed / renovated building
Eco cleaning products
Responsibly sourced firewood
Motion sensor lightbulbs
Public transport accessible
In the heart of Helmsley, on the Cleveland Way sits a beautiful stone barn that’s been lovingly renovated into a charming cottage for two. This peaceful retreat offers couples a romantic base from which to explore the stunning Yorkshire countryside around them, as well as the beautiful market town in which the cottage sits.
From the outside, the home has that quintessential British cottage feel with beautiful stonework on display. And, when you step inside it exudes that same simple charm, with whitewashed walls, exposed wooden beams and a cosy log-burning fireplace keeping things toasty and warm.
The open plan living space features a quaint kitchenette, with modern appliances and some comfy seating around a cute coffee table. This is a lovely spot to enjoy that first cuppa of the morning as you plot the day ahead. You can also settle in here, warming your toes in front of the flames as you tuck into a good book. This space is also bright and airy and offers direct access to the outdoor space.
On warm summer days, you can also sit in the charming courtyard garden catching up with your loved one on the garden bench or enjoy a peaceful lunch at the small alfresco table for two. This is little suntrap is another great spot for a morning coffee and is just as good for observing the Dark Skies above.
When night falls, head to the cosy king size bedroom which features the building’s original stone wall and has exposed wooden beams that create a great sense of character and old world charm. The super-comfy bed offers a restful night’s sleep and the ensuite bathroom features a modern shower.
Helmsley, on the edge of the North York Moors, is a charming market town of stone cottages, cobbled streets and cosy inns. Wander its market square, explore Helmsley Castle and the beautiful walled gardens, or sample local produce in delis and tearooms. Venture further to discover the haunting ruins of Rievaulx Abbey, the wild trails of the Cleveland Way and the dramatic Yorkshire coast, from Whitby’s gothic charm to the windswept beauty of Robin Hood’s Bay.
Please note that the minimum stay for this property is 3 nights
Little Barn Helmsley is owned and managed by Helen.
You can ask a question or make a booking request directly with Helen.
From £400 for a 3 night stay (inclusive of laundry and cleaning fee).
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The cottage sits in the heart of Helmsley, right on the Cleveland Way, offering a peaceful and romantic base to explore the North York Moors and the beautiful Yorkshire countryside.
Check-in is from 3pm and check-out is by 10am. You’ll receive full details, directions and the lock box code 1–2 days before arrival.
Yes, guests can park directly in front of the barn. Please be careful not to block the neighbouring driveway, as it must remain clear at all times.
Unfortunately, pets are not permitted at the property.
The kitchenette includes an oven, 2-ring induction hob, fridge (no freezer), toaster, kettle and cafetiere — ideal for preparing simple meals and morning coffee.
Yes, there’s full fibre WiFi (Swish Fibre). Mobile signal can be limited, so we recommend using WiFi calling for best results.
There’s a smart TV (no aerial) so you can stream your favourite shows using your own app log-ins such as BBC iPlayer or Netflix.
The cottage has electric radiators in the living area and bedroom, underfloor heating and a heated towel rail in the bathroom, plus a cosy log burner with a small starter pack of logs (October to April).
Yes, an external drying store is provided for muddy boots, coats and outdoor kit — perfect after a day on the Cleveland Way.
You can contact the owner through the ‘Request to Book’ button on the Coolstays listing. From there, you can enquire about dates, message the owner directly and book your stay.