Helmsley Cottages
This charming market town nestled in the rolling hills of North Yorkshire, offers a perfect blend of history, culture, and natural beauty. With its picturesque streets lined with historic buildings, quaint shops, and welcoming cafes, it's the ideal destination for a leisurely retreat. Whether you're exploring the imposing ruins of Helmsley Castle, strolling through the peaceful grounds of Duncombe Park, or indulging in a spot of retail therapy at the town's boutique shops, there's something for everyone to enjoy. Plus, with its proximity to the stunning North York Moors National Park, outdoor enthusiasts can take advantage of the numerous walking trails and scenic viewpoints nearby. And don't forget to sample some local delicacies at one of Helmsley's charming eateries before you leave. Looking for your next home away from home, then search our selection of Helmsley cottages for inspiration.
Popular Helmsley Cottages
- Sleeps up to 6
- 3 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.5
out of 5
7 nights
From
- Sleeps up to 6
- 3 bedrooms
- 3 bathrooms
- Up to 1 pet allowed
4.2
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
5
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
4.5
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
4.9
out of 5
7 nights
From
- Sleeps up to 5
- 2 bedrooms
- 1 bathroom
- Up to 0 pets allowed
4.8
out of 5
7 nights
From
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
Dog Friendly Helmsley Cottages
- Sleeps up to 6
- 3 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.5
out of 5
7 nights
From
- Sleeps up to 6
- 3 bedrooms
- 3 bathrooms
- Up to 1 pet allowed
4.2
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
5
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
4.5
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
4.9
out of 5
7 nights
From
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
4.4
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
4.9
out of 5
7 nights
From
Luxury Helmsley Cottages
- Sleeps up to 6
- 3 bedrooms
- 3 bathrooms
- Up to 1 pet allowed
4.2
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.6
out of 5
7 nights
From
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
- Sleeps up to 6
- 4 bedrooms
- 4 bathrooms
- Up to 2 pets allowed
4.5
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 3 bathrooms
- Up to 0 pets allowed
3
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
5
out of 5
7 nights
From
- Sleeps up to 8
- 4 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
Romantic Helmsley Cottages
- Sleeps up to 6
- 3 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.5
out of 5
7 nights
From
- Sleeps up to 6
- 3 bedrooms
- 3 bathrooms
- Up to 1 pet allowed
4.2
out of 5
7 nights
From
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
4.5
out of 5
7 nights
From
- Sleeps up to 5
- 2 bedrooms
- 1 bathroom
- Up to 0 pets allowed
4.8
out of 5
7 nights
From
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 0 pets allowed
4.9
out of 5
7 nights
From
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
Inspiration of things to see and do in our cottages in Helmsley
This picturesque market town in North Yorkshire offers a blend of history, natural beauty, and charming attractions. With the largest collection of Yorkshire cottages, we have the perfect home away from home for you.
Here are the top five things to see and do in our cottages in Helmsley:
Helmsley Castle
Explore Helmsley Castle, a medieval fortress with well-preserved ruins. Climb to the top of the tower for panoramic views of the town and the surrounding countryside.
Rievaulx Abbey
Visit Rievaulx Abbey, a stunning Cistercian monastery located just a short drive from Helmsley. Walk among the atmospheric ruins and appreciate the tranquillity of this historic site.
Duncombe Park
Discover Duncombe Park, a magnificent stately home surrounded by beautiful gardens and parkland. Take a leisurely stroll through the landscaped grounds and enjoy the peaceful atmosphere.
Helmsley Walled Garden
Enjoy the beauty of Helmsley Walled Garden, a five-acre site restored to its former glory. The garden features a wide variety of plants, flowers, and themed areas to explore.
North York Moors National Park
Explore the stunning landscapes of the North York Moors National Park, which surrounds Helmsley. Go for scenic walks, enjoy cycling routes, or simply appreciate the beauty of this expansive national park.
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