
Holiday rentals in Helmsley
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Top-rated holiday rentals in Helmsley
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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 with a safe garden for dogs and children. The Forresters Arms, serving local ales and meals, is a mere 20m across the square, it is best to reserve a table. The Mouseman Furniture Centre is just around the corner and the White Horse of Kilburn is a good walk up the hill.

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.

Renovated 16th century haven in North Yorks Moors
Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

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!

Gorgeous country cottage in a stunning location
A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

Couple's Bothy near Helmsley in the National Park
Unwind at this unique and tranquil getaway. Our converted barn offers a cosy, self-catering retreat for two with a woodfired hot tub, on our remote, but accessible farm in the North York Moors National Park. The Bothy is a self-contained, open space providing king sized bed, ensuite, kitchen, sitting area, outside terrace sun trap & free WiFi. The Bothy has been completed to an exceptionally high standard combining beautiful detailing and practicality. A great location for walking & cycling.

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.

Unique and Cosy Cruck Cottage
Cruck Cottage is in the pretty village of Wombleton, close to the market towns of Helmsley and Kirkbymoorside, on the edge of the North Yorkshire Moors National Park. You will have off street parking and a private patio with seating area and BBQ. The 15C Plough pub (Good Food Guide listed) is just a short walk away. We are ideally located with easy access to the beautiful North York Moors National Park, James Herriot Country, Whitby and the spectacular North Yorkshire coastline.

Maltkiln House Annexe North Yorkshire moors
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. We are also very close to some great pubs and restaurants.

Mill House Annex, Oldstead
This bolthole has been lovingly refurbished to a high standard throughout, providing guests with a comfortable and cosy home-from-home. There is a spacious bedroom with a king-size bed, a modern bathroom fitted with underfloor heating and a sperate bath and shower. The living room has a cosy log fire and large dining table. The kitchen is well appointed and kitted out to meet all your culinary needs. Take it easy at this unique and tranquil getaway.

The Flat @ 2 Castlegate
Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

Garden Cottage - Peaceful in the Heart of Helmsley
A Unique Self-Catering Experience ! Stay in your own private luxury Home-from-Home private cottage, attached to our 1560-Built property opposite the Market square. Your own private entrance leads into your own Dining Room and Kitchenette area which leads into your own large separate Lounge. A well-appointed Shower Room is situated on the ground floor. Upstairs is a large Bedroom with fitted wardrobes and TV.
Popular amenities for Helmsley holiday rentals
Other great holiday rentals in Helmsley

Honeysuckle Cottage

Fairfax View - delightful annexe cottage, Gilling

Little Barn Helmsley

The Helmsley Hut

Fox Cottage in lovely Helmsley

Crumbleclive Cabin

Romance or a rest at The Nest Castleton,Whitby!

Old Forge in Wrelton, North Yorkshire.
When is the best time to visit Helmsley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £103 | £108 | £114 | £124 | £143 | £120 | £142 | £140 | £131 | £111 | £108 | £106 |
| Avg. temp | 4°C | 5°C | 6°C | 9°C | 12°C | 15°C | 17°C | 16°C | 14°C | 10°C | 7°C | 4°C |
Frequently Asked Questions
What are the most popular amenities for Cottage Rentals in Helmsley?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in cottage rentals in Helmsley?
Experience the best of Helmsley with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Helmsley have a kitchen?
Absolutely! We offer over 30 cottage rentals with a kitchen in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Helmsley?
Four-legged friends are welcome in Helmsley. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Helmsley?
Yes! Work meets play with ease at over 20 vacation rentals in Helmsley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Helmsley have free parking?
Absolutely! We offer over 10 house rentals with free parking in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Helmsley have wifi?
Absolutely! We offer over 30 cottage rentals with wifi in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Helmsley?
Helmsley has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
All about Helmsley
Nestled amid the 554 square miles of the North York Moors National Park, Helmsley — located on the banks of the River Rye — is the quintessential English market town, boasting cobbled market squares, honeyed-stone cottages, historic inns, and 51 listed buildings, all looked over by the ancient ruins of the 12th-century Helmsley Castle. Circled by the most wondrous countryside, Helmsley really is the perfect place to base yourself as you explore the glories of the surrounding landscape: Two of the finest trails in the United Kingdom, The Cleveland Way and the Ebor Way, both start in the town. The town comes to life on market day (Friday), when hundreds of independent traders descend to peddle their wares. But if the hustle and bustle gets to be too much, there’s also a heated outdoor community pool to enjoy in the summer months.
What are the top things to do in Helmsley?
Helmsley Castle
First built around 1120, this castle has lived many lives. Initially designed as a defensive fortress, it became an elaborate Tudor mansion, then a Civil War stronghold, and later a romantic Victorian ruin. Now you can enjoy a hands-on exhibition illustrating its many guises and an audio tour of the site. Beside the castle is Helmsley Walled Garden, a beautifully restored 18th-century garden that is an oasis of tranquility.
Rievaulx Abbey
Just a couple of miles from Helmsley Castle (there’s a trail taking you on a scenic route from one site to the other) are more impressive ruins, though of a more ecclesiastical nature. Rievaulx Abbey was once one of England’s most powerful Cistercian monasteries before being dissolved by Henry VIII in 1538. A detailed audio tour highlights the fascinating history of this very special place.
Nunnington Hall
One of the finest manor houses in the United Kingdom is only 6 miles southeast of Helmsley. Erected in the 17th century and now maintained by the National Trust, Nunnington Hall features a delightful walled garden where peacocks stroll. As well as the wonderful period rooms and an astonishing collection of miniature rooms, the Hall also stages contemporary art and photography exhibitions.
Quick stats about holiday rentals in Helmsley

Total holiday rentals
Explore 50 holiday rentals in Helmsley

Nightly prices starting at
Helmsley holiday rentals start at £82 per night before taxes and fees

Verified guest reviews
Over 1,970 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Helmsley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Helmsley rentals

4.8 Average rating
Helmsley stays are highly rated by guests – averaging 4.8 out of 5!
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