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.

Meadow Spa Cabin - Helmsley
No reviews

Meadow Spa Cabin

cabin, Helmsley
Meadow Spa Cabin is a secluded holiday home located in Helmsley, 55 kilometers from Teesside International Airport and adjacent to Helmsley Meadows.
This one-bedroom lodge, spanning 35 square meters, accommodates two guests and features a private entrance, a fully equipped kitchen, a sauna, a hot tub, a sun terrace, and free WiFi.
The Cottage Gillamoor - Helmsley
9.6 61 reviews

The Cottage Gillamoor

house, Gillamoor
The Cottage Gillamoor is situated on a quiet street in Gillamoor, around 19 kilometres from Flamingo Land Theme Park and 26 kilometres from Dalby Forest. This house has received excellent ratings for its location, cleanliness and overall user experience.
The property has two bedrooms and one bathroom, with a floor area of 40 square metres and a guest capacity of four. The Cottage Gillamoor offers a range of amenities, including a fully equipped kitchen, a terrace with garden views, a spa, a restaurant, a tennis court, and a children’s playground.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Helmsley
No reviews

Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Helmsley
Willow Cottage is a charming 2-bedroom house located just a 3-minute walk from Helmsley's Market Place, with easy access to shops, restaurants, and bars. This peaceful location offers a great base for exploring the historic market town and the surrounding Yorkshire countryside.
The house is perfect for families or groups of up to 4 guests, with a spacious open-plan kitchen and dining area, a modern bathroom, and a tranquil garden with a patio. Guests can enjoy the fully equipped kitchen, relax in the comfortable living room with its original beams and exposed brick fireplace, and make the most of the enclosed garden with its outdoor dining area and garden arbour seat.
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.

Best family friendly Helmsley holiday rentals

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

2 Bed In York (Oc-93614) - Helmsley
10 1 review

2 Bed In York (Oc-93614)

apartment
This two-bedroom cottage in Nawton, North Yorkshire, is situated 0.8 kilometres from a pub and restaurant, 4.8 kilometres from a shop, and offers proximity to Yorkshire Lavender Farm, Byland Abbey, and Sutton Bank National Park Centre.
This pet-friendly family accommodation sleeps up to three guests and features a garden with a pond and BBQ, a lounge with an electric fire, and a country-style kitchen, making it ideal for those seeking a relaxing rural retreat.
The Coach House - Helmsley
10 4 reviews

The Coach House

house
The Coach House, a self-catering property in Bilsdale, North Yorkshire, is situated six miles (approximately 9.6km) north of Helmsley, within the North Yorkshire Moors National Park.
This two-bedroom dwelling, sleeping up to four guests, offers an open-plan kitchen/living area, a garden, parking, and access to Freeview TV and streaming services; breakfast and dinner hampers are available upon pre-booking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Helmsley
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Helmsley
Lily Pad Cottage, a two-bedroom holiday home in Helmsley, North Yorkshire, is situated a minute's walk from the town centre, Helmsley Castle, and the Helmsley Walled Garden.
This self-catering property sleeps four, offering a modern kitchen-diner with dishwasher and washer-dryer, a cosy living room with wood-burning stove, two bedrooms with Smart TVs, a family bathroom, private parking, and a patio; travel cot and highchair are available.
Host & Stay - Anvil Cottage - Helmsley
8.7 6 reviews

Host & Stay - Anvil Cottage

house, Kirkbymoorside
Anvil Cottage, a 2-bedroom house in Kirkbymoorside, North Yorkshire, offers easy access to Dalby Forest (24km), Flamingo Land Theme Park (14km), and Helmsley Castle (10km).
This 64 square metre property sleeps 5, features a fully equipped kitchen with fridge and microwave, a washing machine, free Wi-Fi, and a private entrance.

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

Saxon House - Helmsley
10 2 reviews

Saxon House

house, Harome
Saxon House, a five-bedroom property in Harome, North Yorkshire, is situated 22.5km from Flamingo Land and 29km from Dalby Forest.
This large house sleeps 17 guests, boasting three bathrooms, two living rooms, a garden, free Wi-Fi, parking, and is ideally located for exploring the North Yorkshire Moors National Park.
2 Bedroom Quiet Cottage Gillamoor North York Moors - Helmsley
9.5 13 reviews

2 Bedroom Quiet Cottage Gillamoor North York Moors

apartment
This modernised two-bedroom farm cottage in the North York Moors village of Gillamoor offers easy access to attractions such as York (approx. 60km), Scarborough (approx. 50km), Whitby (approx. 40km), Castle Howard, Flamingo Land, and Rievaulx Abbey.
The property sleeps four, boasts a fully equipped kitchen (fridge, freezer, microwave), free WiFi, a cosy log burner, private garden, parking, and provides access to Dalby Forest's extensive walking and cycling paths, along with binoculars, torches, and bird food for nature enthusiasts.
Cliff Stud Retreat, Helmsley - Cecil Cottage - Helmsley
9.7 154 reviews

Cliff Stud Retreat, Helmsley - Cecil Cottage

apartment
Cecil Cottage is situated on a 220-acre estate, just a short walk from the centre of Helmsley, a charming market town in the North York Moors National Park. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is a comfortable three-bedroom property that can accommodate up to five guests. It features a fully equipped kitchen, a modern bathroom, a cosy living room with Sky TV and a private garden with fruit trees. Guests also have access to the estate's extensive grounds, offering opportunities for walks and exploring the surrounding countryside.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Helmsley
9.0 7 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Helmsley
This stone holiday home is located in Helmsley, 500 meters from Helmsley Castle and 1.5 kilometers from Duncombe Park.
The four-bedroom property sleeps eight guests and offers a sleek kitchen, a lounge with a wood burner, and an outdoor BBQ area, with parking for two cars and Wi-Fi available.

Neighborhoods and points of interest in Helmsley

Best Helmsley holiday rentals with a sauna

Meadow Spa Cabin - Helmsley
No reviews

Meadow Spa Cabin

cabin, Helmsley
Meadow Spa Cabin is a secluded holiday home located in Helmsley, 55 kilometers from Teesside International Airport and adjacent to Helmsley Meadows.
This one-bedroom lodge, spanning 35 square meters, accommodates two guests and features a private entrance, a fully equipped kitchen, a sauna, a hot tub, a sun terrace, and free WiFi.

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.

Cottage ∙ 3 Bedrooms ∙ 5 Guests - Helmsley
9.6 34 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, 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.

Beautiful Stone Cottage In The Heart Of Helmsley - Sleeps 2 - Helmsley
No reviews

Beautiful Stone Cottage In The Heart Of Helmsley - Sleeps 2

apartment, Helmsley
The Pheasant Apartment, Helmsley - Helmsley
10 1 review

The Pheasant Apartment, Helmsley

apartment, Helmsley
Clematis Cottage @ Coach House Cott - Helmsley
9.8 48 reviews

Clematis Cottage @ Coach House Cott

apartment
Isca Lodge, Wombleton - Helmsley
No reviews

Isca Lodge, Wombleton

chalet, York

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.

Cliff House - Helmsley
9.2 14 reviews

Cliff House

house, York

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.

Crossing Cottage - Helmsley
9.9 27 reviews

Crossing Cottage

house, Helmsley
The Old Bank Apartments, Helmsley, North Yorkshire - Helmsley
10 1 review

The Old Bank Apartments, Helmsley, North Yorkshire

apartment, Helmsley
Sugi Pod, Hinoki Retreat, Newburgh Priory Estate - Helmsley
9.9 532 reviews

Sugi Pod, Hinoki Retreat, Newburgh Priory Estate

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

The Partridge Apartment, The Old Bank, Helmsley

apartment, Helmsley
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