Holiday Rentals in Helmsley

119 available vacation rental offers

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Helmsley holiday rentals
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Best Holiday rentals and Airbnb offers in Helmsley

Guest-Favourite Self-Catering Rentals with a Balcony in Helmsley

Morning coffee with views across the hills is a simple pleasure in these holiday rentals in Helmsley. Each option features a beautiful outlook.

Cavendish Court - Helmsley
9.9 145 reviews

Cavendish Court

house, York
Cavendish Court, near York, offers a self-catering property 16km from Flamingo Land and 29km from York Minster, providing convenient access to both attractions.
This 74 square metre house sleeps four, featuring two bedrooms, a bathroom with washing machine, a fully equipped kitchen with dishwasher, a living room with flat-screen TV, free Wi-Fi, private parking, and a garden with outdoor dining area; ideal for cycling and hiking.
Waters Edge Cabin - Helmsley
No reviews

Waters Edge Cabin

cabin, Helmsley
Waters Edge Cabin, a self-catering lodge, is located in Helmsley, approximately 53 kilometres from Teesside International Airport.
This one-bedroom, one-bathroom cabin accommodates two guests, offering 30 square meters of space with a fully equipped kitchen, outdoor hot tub, sun terrace, barbecue facilities, free WiFi, and private parking.
The Old Bank Apartments - Helmsley
No reviews

The Old Bank Apartments

apartment, Helmsley
The Old Bank Apartments are located in Helmsley, providing convenient access to local attractions and amenities.
This family-friendly flat offers a kitchen with a fridge, microwave, and dishwasher, a Jacuzzi, a terrace/balcony, a tennis court, and on-site parking, with free Wi-Fi and concierge services available.
Keld Spring Lodge Retreat - Helmsley
8.0 26 reviews

Keld Spring Lodge Retreat

resort, Helmsley
Keld Spring Lodge Retreat is located in Helmsley, North Yorkshire, approximately 19km from Flamingo Land Theme Park and 29km from York Minster.
This self-catering lodge offers two bathrooms, free Wi-Fi, and free private parking, with some units including fully equipped kitchens; nearby attractions include Dalby Forest (29km) and Spa Scarborough (47km).

Best family friendly Helmsley holiday rentals

Among the 119 accommodations in Helmsley, here are the 4 best family friendly rentals

Saxon House, Harome, North York Moors - Helmsley
9.7 7 reviews

Saxon House, Harome, North York Moors

apartment, Harome
Saxon House, a dog-friendly detached stone property in Harome, North Yorkshire, is situated near the acclaimed restaurants The Pheasant and The Star Inn at Harome, and within easy reach of the North York Moors National Park.
This five-bedroom house, with a self-contained annexe, sleeps nine guests and offers a 1 square metre floor area, a well-equipped kitchen with dishwasher, ample parking, a south-facing garden, and a wood-burning stove; a high chair and travel cot are provided.
Cottage In Wass, Near Ampleforth - Helmsley
10 1 review

Cottage In Wass, Near Ampleforth

cottage
This country cottage is situated in Wass Village, within the North Yorkshire Moors National Park and Area of Outstanding Natural Beauty, a 5-minute walk from Wass Bank.
The accommodation sleeps six guests in three bedrooms, featuring two bathrooms, a gated garden with a BBQ, and is located opposite The Stapylton Arms Pub.
4 Bed In Helmsley (Oc-l29736) - Helmsley
8.0 1 review

4 Bed In Helmsley (Oc-l29736)

apartment
This stone cottage is located in Hemsley, North Yorkshire, 800 metres from Helmsley Castle and 2.4 kilometres from Duncombe Park, with the North York Moors National Park also nearby.
This family-friendly, 4-bedroom holiday home accommodates up to 8 guests and features a well-equipped kitchen with a microwave, a wood burner, a utility room with a washer/dryer, a patio with BBQ and fire pit, and private parking for two cars, allowing one dog per booking.
Ivy Cottage - Helmsley
9.2 11 reviews

Ivy Cottage

house, Helmsley
Ivy Cottage is situated in Helmsley, just a short walk from Helmsley Castle and a 48-kilometre drive from Lightwater Valley Theme Park, making it an ideal base for exploring both the town and the surrounding countryside. Guests have consistently rated the cottage as excellent for its cleanliness, location, and overall experience.
The cottage has three bedrooms and one bathroom, offering comfortable accommodation for up to five guests in a 130 square metre space. Amenities include a fully equipped kitchen, a garden, free Wi-Fi, and parking, ensuring a pleasant and convenient stay.

Frequently asked questions about holiday rentals in Helmsley

  • What are some interesting places to visit in or near Helmsley?

    Helmsley Castle is a must-see, it's a 12th-century castle with impressive ruins. The Ryedale Folk Museum is great for learning about the local history and there's the beautiful Helmsley Walled Garden with its stunning displays.
  • What are the best Airbnb and holiday rentals in Helmsley?

  • Which walking or cycling routes are the best in Helmsley?

    The Cleveland Way National Trail passes through Helmsley, offering fantastic views. The 10-mile Helmsley to Rievaulx Abbey cycle route is popular and the 6.5-mile Helmsley Circular Walk is great for a shorter stroll.
  • What are the most popular Airbnbs in Helmsley?

  • What sports or outdoor activites can visitors enjoy in and around Helmsley?

    You can go fishing at the River Rye, there's a golf course at Helmsley, and you can go horse riding at one of the local riding schools. The area is also great for birdwatching.
  • What are the best holiday rentals with a pool in Helmsley?

    The best holiday rental with a pool in Helmsley is The Helmsley Retreat.

  • What other towns or cities can be easily accessed from Helmsley?

    You can easily get to York, which is about 40km away, and the historic city of Whitby is about 60km away. The market town of Pickering is only 10km away and is worth a visit.
  • What are the best rentals for families and kids in Helmsley?

  • What amenities are commonly available in vacation rentals in Helmsley?

    Most vacation rentals in Helmsley will have kitchens, bathrooms, and living areas. Many will also have Wi-Fi, TVs, and washing machines. Some may have gardens or patios too.
  • What are the best rentals or Airbnbs with a jacuzzi in Helmsley?

    The best holiday rentals or Airbnb with a jacuzzi in Helmsley are The Pheasant, Crossing Cottage and The Old Bank.

  • What time of year is best to rent a vacation rental Helmsley?

    The best time to visit Helmsley is during the spring or summer months when the weather is warmer and the days are longer. Autumn is also beautiful with the changing colours of the leaves.
  • What are the local dishes in Helmsley region?

    You should try the Yorkshire Pudding, a traditional dish made with batter and served with roast beef. The local cheeses are also delicious, especially Wensleydale cheese.

Popular destinations

Best Helmsley holiday rentals with a fireplace

Hideaway Cottage - Helmsley
8.0 9 reviews

Hideaway Cottage

apartment
Hideaway Cottage is a two-bedroom holiday let located in Ampleforth village, 31 kilometres from the historical city of York.
This pet-friendly cottage accommodates four guests and features a well-equipped kitchen with a dishwasher, a living room with a log burner, and a private terraced garden with direct access to walking trails.
Holly Cottage - Helmsley
No reviews

Holly Cottage

apartment
Holly Cottage, a holiday cottage in Harome, is located near Beadlam and offers a rural retreat.
This property accommodates up to six guests in three bedrooms, features a well-equipped kitchen with a dishwasher, a sitting room with a woodburning stove, and a garden with a patio, all within 500 meters of local amenities, and allows pets.
Pear Tree Cottage @ Coach Cottages - Helmsley
9.9 34 reviews

Pear Tree Cottage @ Coach Cottages

apartment
This Pear Tree Cottage is located in Gilling East, North Yorkshire, Great Britain, offering convenient access to the historic city of York (approximately 45 kilometres away) and the North Yorkshire Moors.
This family-friendly two-bedroom, one-bathroom apartment accommodates up to four guests and features a kitchen with a fridge, microwave, and dishwasher, along with a garden, parking, and an on-site tennis court.
Saxon House (7) - Helmsley
10 2 reviews

Saxon House (7)

apartment
Saxon House, in the North Yorkshire village of Harome, is ideally located next to The Pheasant and The Star Inn, two Michelin-starred restaurants.
This five-bedroom house, sleeping nine, boasts a spacious open-plan kitchen/dining area, a triple-aspect sitting room with a wood-burning stove, a generous enclosed garden, and ample parking, plus an annexe available for larger groups; a highchair and travel cot are provided (linen not included).

Neighborhoods and points of interest in Helmsley

Best Helmsley holiday rentals with a sauna

Ashberry Glamping Pod - Helmsley
8.9 6 reviews

Ashberry Glamping Pod

glamping, York
Ashberry Glamping Pod, near York, offers a peaceful retreat approximately 29 kilometres from Flamingo Land and 30 kilometres from York Minster.
This one-bedroom pod sleeps three, features a 18 square metre floor area, includes free Wi-Fi and private parking, and provides an outdoor dining area.

Top-Rated 5-Star Self-Catering Holiday Rentals in Helmsley

A mountain luxury holiday rental or Airbnb in Helmsley sets the right tone from the moment you arrive with 5-star comfort. Explore our top-rated stays.

Campion Cabin - Helmsley
No reviews

Campion Cabin

cabin, Helmsley

Find the Best Pet-Friendly Holiday Rentals in Helmsley

No need to leave the dog behind in Helmsley. These holiday rentals offer dog-friendly trails and plenty of space to roam. Start planning now.

Holly Cottage, Pet Friendly, Character Holiday Cottage In Helmsley - Helmsley
No reviews

Holly Cottage, Pet Friendly, Character Holiday Cottage In Helmsley

cottage, York
A Holiday Cottage That Sleeps 10 Guests  In 5 Bedrooms - Helmsley
No reviews

A Holiday Cottage That Sleeps 10 Guests In 5 Bedrooms

cottage, York
Saxon House - Helmsley
10 2 reviews

Saxon House

house, Harome
4 Bed In Helmsley (Oc-l29736) - Helmsley
No reviews

4 Bed In Helmsley (Oc-l29736)

cottage, Helmsley

Handpicked Self-Catering Rentals with a Pool in Helmsley

These holiday rentals in the hills around Helmsley include a pool, so a refreshing dip after a long walk is always an option.

2 Bed In York Oc-81052 - Helmsley
No reviews

2 Bed In York Oc-81052

house, Helmsley

Choose the Right Holiday Rentals with a Hot Tub in Helmsley

Coming back to a hot tub after a day in the hills changes the whole feel of a stay. These holiday rentals in Helmsley are ready for you.

Prestige-appartement-sdb Privée-vue Sur Rue-sleeps - Helmsley
No reviews

Prestige-appartement-sdb Privée-vue Sur Rue-sleeps

apartment
The Coppice Cabin - Helmsley
No reviews

The Coppice Cabin

cabin, Helmsley
The Partridge Apartment, The Old Bank, Helmsley - Helmsley
No reviews

The Partridge Apartment, The Old Bank, Helmsley

apartment, Helmsley
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