#{ServerName}

Helmsley dog-friendly cottages

Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)

Isla Cottage

Osmotherley, North Yorkshire

3
2
1
pets 1
Snug and inviting, this pretty retreat is well-suited for couples or small families wishing to spend some time away from it all in a picturesque rural location on the edge of the North York Moors.
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)

Coco

Helmsley, North Yorkshire

3
2
1
pets 1

A delightful haven on the fringes of the incredible North York Moors, offering friends and family a dreamy escape from the rhythm of everyday life.

Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)

Hare House

Stokesley (2mls SW), North Yorkshire

4
2
1
pets 2

Gorgeous holiday home surrounded by the open countryside, situated on the cusp of the North York Moors National Park, equidistant to quaint villages and vibrant market towns offering attractions aplenty.

Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)

Partridge Cottage - Chopgate

Osmotherley, North Yorkshire

4
2
2
pets 2

Sympathetically converted to retain original brickwork and wooden beams, this rural barn conversion is a stylish bolthole for long walks over the moors.

The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)
The Cottage At Helmsley (40512)

The Cottage At Helmsley

Helmsley, North Yorkshire

4
2
1
pets 1

Pretty stone cottage sleeping four, situated on the edge of the North Yorkshire Moors National Park in the popular market town of Helmsley, with the town’s shops, pubs, and restaurants right on the doorstep.

St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)

St Aidans

Helmsley, North Yorkshire

4
2
2
pets 2

This imaginatively converted Grade II listed former church offers cosy, welcoming and unique accommodation for couples looking for a lovely retreat on the outskirts of the beautiful North York Moors.

Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)

Webstone Cottage

Osmotherley, North Yorkshire

4
2
1
pets 2

This charming cottage with an abundance of character in the North York Moors is an idyllic retreat for families looking to explore the natural treasures in the surrounding countryside.

Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)

Lavender Cottage - Helmsley

Helmsley, North Yorkshire

5
3
1
pets 1
This charming cottage set within the traditional market town of Helmsley is brimming with character and is perfect for a family of walkers wanting to explore the North York Moors National Park.
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)

The Old Hay Barn

Great Busby, North Yorkshire

6
3
1
pets 2
Enjoy relaxing in this countryside retreat on the cusp of the North York Moors. The open-plan space provides the ultimate social accommodation to take a relaxing break with friends or family.
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura
Laura

Laura's Cottage - Helmsley

Helmsley, North Yorkshire

6
3
2
pets 1
With a plethora of places to visit and activities to experience, you are spoilt for choice when it comes to stays in Helmsley. Ideal village centre location for keen walkers, thrill seekers and nature lovers.
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)

Pheasant Cottage - Chopgate

Osmotherley, North Yorkshire

6
3
2
pets 2

The larger of two barn conversions, this beautiful property is perfect for memorable getaways in the North York Moors.

These properties are further afield
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)
Penzola Cottage (G0120)

Penzola Cottage

Rosedale, North Yorkshire

2
1
1
pets 2

This delightful cottage is set in a picturesque village near the centre of the North York Moors and makes a romantic bolthole for a couple looking for a peaceful retreat in lovely rural surroundings.

Dog-friendly self-catering accommodation in Helmsley

Browse our Yorkshire holidays to discover our exclusive range of luxurious pet-friendly and self-catering accommodation. Imagine your ideal escape, sipping a glass of soothing red as you bask in front of a roaring fire, based in a honeyed stone cottage at the heart of one of the prettiest towns in Yorkshire. If this is precisely how you envisage your stay, then our dog-friendly cottages in Helmsley are perfect for you. Our Helmsley dog-friendly holiday cottages are surrounded by the spectacular North York Moors, boasting an abundance of exciting trails to explore, and chocolate-box villages to peruse. The town itself is a hive of cobbled streets, independent shops and quintessential tearooms, overlooked by the impressive ruins of Helmsley Castle.

Don your walking boots or prepare your bicycle for a day of adventures, soaking in the stunning views as you navigate acres of heather-covered heathland. Step back in time as you uncover the secrets of the majestic castle and the ruins of two monasteries, losing yourself in the enchanting walled gardens as you explore. Once you have worked up an appetite, there are plenty of eateries to tantalise your taste buds, followed by a leisurely dip in the heated open-air swimming pool. Venturing slightly further afield, the intrepid explorer will enjoy a day trip to Duncombe Park, home to the National Centre for Birds of Prey, or the delightfully serene Nuneaton Hall on the banks of the River Rye. Discover more to do in Helmsley in our guide

Search
nights
+ / - days
guests
bedrooms
dogs
Filters

Location

  • Beach within 5 miles
  • Pub within 1 mile
  • Waterside views
  • Shop within 1 mile

Facilities

  • Games / Play facilities
  • Tennis court
  • Swimming pool
  • Internet access
  • Sky TV
  • Spa facilities
  • Four poster bed
  • Indoor swimming pool
  • Hot tub
  • Open fire / woodburner
  • Enclosed garden / patio

Property

  • Does not allow pets
  • Quirky
  • Increased accessibility
  • Apartment
  • Downstairs bathroom
  • Luxury
  • Log cabin / Lodge
  • Family friendly
  • Working farm
  • Downstairs bedroom
  • Romantic
  • Shepherd hut
The Travel Chapter Limited, trading as holidaycottages.co.uk | The Travel Chapter Limited is registered in England and Wales. | Registered office Travel Chapter House Gammaton Road Bideford EX39 4DF Company No. 02431506 | VAT reg: 143053210