Pet-friendly vacation rentals in Helmsley

Diamond Den- a quiet, peaceful and private haven.

Situated in the extremely peaceful village of Butterwick, just a few moments walk to the river rye and bridge, Diamond Den is the perfect retreat. Being at the foot of the Howardian Hills provides a wealth of walking opportunities and we are just a short drive away from some spectacular market towns, including Helmsley (8m) Malton( 5.4m), Ampleforth (9.7m) and Pickering (8.5m). You will have your own private garden space and parking. ACCESS TO THE SLEEPING AREA IS UP A LADDER- PLEASE SEE IMAGES

Central Fully Ensuite house sleeps 6 dog friendly

The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.

Historic cottage, log-burning tub & village pub

Unwind in this beautifully restored Grade II listed, 17th Century farmers cottage with exposed beams, original ironwork, underfloor heating and a soothing log burning hot tub. Opposite you'll find a cosy, dog-friendly village pub with open fires. You’ll be 7 minutes away from artisanal food producers in the market town of Malton (known as Yorkshire's Food Capital) and ideally located for exploring the Yorkshire Wolds (2 miles), Howardian Hills (10 miles), York (17 miles) & Beaches (27 miles).

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Maltkiln House Annexe North Yorkshire moors

Get away from it all, unplug and unwind. Maltkiln House Annex is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast.

The Shed, Hovingham, York

An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.

The Little House Peaceful & self-contained

Located in the centre of the lovely village of Kilburn on the edge of the North Yorkshire Moors National Park, the Little House is peaceful, cosy and self-contained, tucked away from the general hustle and bustle of the village. The Forresters Arms, serving local ales and all meals including breakfast, is a mere 20m across the square. The Mouseman Furniture Centre is just around the corner and the White Horse of Kilburn is a good walk up the hill.