Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- The Manor House
- Esk Cottage in Whitby
- Poppy Lodge at Tavern Cottages
- The Bothy
- The White House
- Jasmine Lodge in Fitling
- Sycamore Cottage in Harwood Dale
- Featherstone House in Darlington
- Sunshine Cottage
- Margaret’s in Driffield
- Rose Cottage at Hoxne Cottages
- Castle View
- Park View Cottage
- Ginger Fox Lodge
- Bouquet
- The Twisted Toad
- Burton Fleming
- Virginia Cottage
- Owls Rest
- The Foldyard
- Shepherd's Hut
- Mayflower at Martindale Shepherds Huts
- Oakworth Cottage One
- Harwood Lodge at Harwood Properties
- Woodpecker Cottage
- Baggergate House
- Shirley’s Haven at Emmotland Holidays
- The Granary
- Waterside Lodge Fourteen
- Kingfisher Lodge
Helmsley Holiday Cottages
Our collection of Helmsley holiday cottages puts you right in the heart of the North York Moors National Park. This market town offers cobbled streets lined with independent shops and the imposing ruins of Helmsley Castle dating back to 1120. You'll find excellent walks including the Cleveland Way starting from the town square!
Whether you're travelling as families, couples or groups, our cottages and lodge accommodation cater for every stay. Many properties feature a hot tub for unwinding after exploring Rievaulx Abbey or wandering through Duncombe Park's landscaped gardens. The town's position makes it perfect for discovering Yorkshire's stunning moorland and picturesque villages.
Visitor Rating
4.8
- Luxury hot tub and sauna
- Prime Helmsley market square location
- Pet-friendly with enclosed garden
- Sleeps 4 in comfort
- Premium furnishings throughout
View Cottage
[+] To Favourites
Visitor Rating
5
- Private wood-fired hot tub
- Panoramic North York Moors views
- Luxury glamping lodge experience
- Working farm countryside setting
- Award-winning customer rated property
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Private hot tub with countryside views
- Secluded romantic setting
- Walking distance to footpaths
- Luxurious compact living space
- Close to coast and Dartmoor
View Cottage
[+] To Favourites
Visitor Rating
4.3
- Private hot tub with country views
- Self-contained studio for two guests
- Working farm in National Park
- Moorland walks from the doorstep
- Welcome pack and towels included
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Grade II listed historic farmhouse
- Private hot tub for eight
- Games room with pool table
- Six car private parking
- Yorkshire Dales countryside location
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub in enclosed garden
- Three en-suite bedrooms sleep six
- Two dogs welcome with private field
- Tennis court and billiards room access
- Wood burner in 30-foot living area
View Cottage
[+] To Favourites
Visitor Rating
5
- Enormous luxury house for 18 guests
- Super comfortable king-size beds
- Hot tub with countryside views
- Perfect for family celebrations
- Close to York and Castle Howard
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Log-fired bath for two
- Kingsize bed luxury accommodation
- Woodburner and cosy atmosphere
- North York Moors location
- Private parking included
View Cottage
[+] To Favourites
Visitor Rating
5
- Wood-fired hot tub with views
- Historic 1707 stone cottage character
- Complete off-grid eco-friendly living
- Direct access to moorland walks
- Working farm with sheep cattle
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub
- Spotlessly clean cabin
- Helpful attentive hosts
- Perfect peaceful location
- Cosy woodburning stove
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Wood-fired hot tub
- Spotlessly clean modern interiors
- Walks from the doorstep
- Attentive helpful hosts
- Perfect romantic retreat
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub with countryside views
- Peaceful rural location
- Close to York and Castle Howard
- Thoughtful welcome hamper
- Comfortable and well-equipped accommodation
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub spa bath
- Romantic kingsize bedroom retreat
- Award winning five star rating
- Pet friendly enclosed garden
- North Yorkshire Moors doorstep location
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub for four
- Cosy wood burner atmosphere
- Luxury barn conversion accommodation
- Stunning countryside views daily
- Pet-friendly with secure garden
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub for six
- Ground floor luxury barn conversion
- Half mile from Pickering town
- Enclosed pet-friendly garden space
- Steam railway station walking distance
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub for two
- Handcrafted shepherd's hut design
- Adults-only romantic retreat
- Dog-friendly accommodation included
- North Yorkshire Moors location
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub with views
- Wood burning stove included
- Three bedrooms sleep five
- Dog friendly with paddock
- Direct moorland walk access
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Four-poster beds
- Hot tub in private courtyard
- Huge dining table for gatherings
- Near Castle Howard and York
- Beautiful Georgian property with gardens
View Cottage
[+] To Favourites
- Private hot tub for six
- Rustic barn conversion charm
- Pet friendly countryside retreat
- Five minutes from Easingwold
- Private fire pit and garden
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub for five
- Zero light pollution stargazing
- Working farm with sheep
- Direct cycle route access
- Castle Howard 20 minutes
View Cottage
[+] To Favourites
- Luxury marble finishes
- Private hot tub
- Horse stables available
- Two woodburning stoves
- Near York and National Parks
View Cottage
[+] To Favourites
Visitor Rating
5
- Steam railway views opposite
- Rooftop hot tub terrace
- Three themed bedrooms
- Central Pickering location
- Free parking permit included
View Cottage
[+] To Favourites
Visitor Rating
5
- Stunning countryside views
- Hot tub with pagoda
- Huge kitchen with two dishwashers
- Ground floor disabled access
- High-quality luxury furnishings
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Private hot tub for four
- Boutique luxury interior design
- Castle Howard two miles away
- Enclosed garden with firepit
- Village pub directly opposite
View Cottage
[+] To Favourites
Visitor Rating
5
- 15 minutes from historic York
- Private hot tub with countryside views
- Four-poster bed and luxury bathrooms
- Dog-friendly with enclosed garden
- High-quality finish throughout
View Cottage
[+] To Favourites
- Private hot tub on decking
- Three bedrooms sleeping six guests
- PlayStation 4 and Smart TVs
- Welcomes up to three dogs
- Near Flamingo Land theme park
View Cottage
[+] To Favourites
Visitor Rating
4
- Private hot tub for six
- Shared swimming pool access
- Xbox One gaming console
- Pet-friendly at no cost
- Nine miles from York
View Cottage
[+] To Favourites
- Sleeps 15 across six bedrooms
- Shared pool, hot tub and sauna
- North Yorkshire Moors National Park location
- Private parking for five cars
- Welcomes up to three dogs
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private secluded garden
- Hot tub under the stars
- Minutes from Malton town centre
- Comfortable king-size bed
- Easy access to York
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub
- Games room with pool table
- Accessible ground-floor bedroom
- Working farm location
- Perfect for family gatherings
View Cottage
[+] To Favourites
Explore more of Vale of York
Popular towns and villages in and around Helmsley