Vacation Rentals in Helmsley

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Helmsley holiday rentals
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119 Holiday rentals and Airbnb in Helmsley

Award-Winning Family Holiday Rentals in Helmsley, United Kingdom

Find family mountain holiday rentals in Helmsley, United Kingdom with room for the whole family.

St Anthonys, Bright Perkily Decorated 3 B/r House - Helmsley
9.8 233 reviews

St Anthonys, Bright Perkily Decorated 3 B/r House

apartment
This pet-friendly Ampleforth holiday home is situated in the village of Ampleforth, North Yorkshire, within walking distance of Ampleforth College and a short drive (approximately 72km) from York.
The three-bedroom property, sleeping up to five guests, boasts a fully equipped kitchen with dishwasher, a wood-burning stove, stunning valley views from its garden, and excellent gastro pubs nearby.
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.
2 Bedroom Accommodation In Helmsley - Helmsley
No reviews

2 Bedroom Accommodation In Helmsley

cottage, Helmsley
Lily Pad Cottage, a two-bedroom Helmsley holiday home, is situated a minute's walk from Helmsley town centre, close to Helmsley Castle and the Helmsley Walled Garden.
This self-catering property sleeps four, boasting a fully equipped kitchen/diner with patio doors leading to a private garden, two bedrooms with Smart TVs (one zip-and-link kingsize bed), a bathroom, plus amenities including gas central heating, Wi-Fi, a travel cot and highchair, and private parking.
Cliff Stud Retreat, Helmsley, Frankel Cottage - Helmsley
9.8 152 reviews

Cliff Stud Retreat, Helmsley, Frankel Cottage

apartment
This charming cottage is located just outside the centre of Helmsley, a short walk from the town's attractions and surrounded by picturesque countryside. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property features three bedrooms and one bathroom, accommodating up to five guests. The cottage is fully equipped with everything you need for a comfortable stay, including a modern kitchen, a cosy living room with Sky TV and Wi-Fi, a private garden, and parking.

Top-Rated Holiday Rentals with a Balcony in Helmsley, United Kingdom

Take in sweeping, uninterrupted alpine valley vistas right from your private mountain rental balcony in Helmsley, United Kingdom.

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.
Campion Cabin - Helmsley
No reviews

Campion Cabin

cabin, Helmsley
Campion Cabin is located in Helmsley, 55 kilometers from Teesside International Airport, offering a secluded retreat near Helmsley Castle and Rievaulx Abbey.
This 30 square meter log cabin accommodates two guests and features a private entrance, a fully equipped kitchen, a hot tub, and a sun terrace, with barbecue facilities and outdoor seating for al fresco dining.
The Old Bank Apartments, Helmsley, North Yorkshire - Helmsley
10 1 review

The Old Bank Apartments, Helmsley, North Yorkshire

apartment, Helmsley
This luxury Georgian townhouse apartment offers an unrivalled position overlooking Helmsley's market square, formerly the town's old bank, with direct access to the North York Moors National Park, 500 meters from Helmsley Castle and 1.5 kilometers from Duncombe Park.
This family-friendly accommodation sleeps up to 10 guests across three bedrooms and four bathrooms, featuring elegant furnishings, high-specification appliances, an optional eight-person hydro pool hot tub on the terrace, and facilities for shooting enthusiasts, with parking and a garden available.
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.

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 Norman castle with a rich history. You can also visit the Ryedale Folk Museum, which showcases the history of the local area. If you're looking for something a bit different, the Duncombe Park is a beautiful estate with a deer park and gardens.
  • What are the best Airbnb and holiday rentals in Helmsley?

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

    The Cleveland Way is a long-distance footpath that passes through Helmsley, offering stunning views of the North York Moors. For cycling, the Helmsley to Pickering cycle path is a popular choice, following the old railway line. You can also explore the many quiet country lanes around the town.
  • What are the most popular Airbnbs in Helmsley?

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

    There are plenty of opportunities for outdoor activities in and around Helmsley. You can go horse riding, fishing, or even try your hand at clay pigeon shooting. There's also a golf course just outside the town.
  • 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?

    York is about a 45-minute drive from Helmsley, and is a great day trip for exploring its historic streets and attractions. You can also easily reach Whitby, Scarborough, and the North York Moors National Park.
  • 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 come with basic amenities like a kitchen, bathroom, and bedrooms. Many also have a garden or patio, and some even have a hot tub or swimming pool. You can often find rentals with Wi-Fi and parking as well.
  • 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 depends on your preferences. Spring and autumn offer mild weather and fewer crowds, while summer is ideal for enjoying the outdoors. Winter can be chilly, but it's a great time to see the moors covered in snow.

Popular destinations

Top-Rated Holiday Rentals with a Sauna in Helmsley, United Kingdom

Melt away your hiking fatigue and sweat out the trail dust at mountain holiday rentals featuring a private sauna in Helmsley, United Kingdom.

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 Holiday Rentals with a Fireplace in Helmsley, United Kingdom

Share stories and roast marshmallows over a roaring hearth after a long day on the trails at mountain rentals with a fireplace in Helmsley, United Kingdom.

Ryegate Cottage - Helmsley
9.0 1 review

Ryegate Cottage

house, Helmsley
This 2-bedroom holiday cottage in Helmsley is located 24 kilometres from Flamingo Land Theme Park and 30 kilometres from Dalby Forest, with York Minster 37 kilometres away.
The property offers accommodation for up to 7 guests, featuring a fully equipped kitchen, 2 bathrooms, and a private garden, with private parking available at an extra cost.
Beadale Cottage - Helmsley
10 6 reviews

Beadale Cottage

house, Ampleforth
Beadale Cottage is located in Ampleforth, a charming village just 32 kilometres from York Minster and York Train Station. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom property is ideal for families or groups of friends, with a total floor area of 1 square metre. Enjoy the spacious living areas, the private garden, free Wi-Fi, and parking, as well as the convenience of a fully equipped kitchen and a comfortable living room with a TV and DVD player.
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.
3 Bed In Helmsley Oc-82891 - Helmsley
8.7 3 reviews

3 Bed In Helmsley Oc-82891

house, Helmsley
This 3-bedroom house is located in Helmsley, just 24km from Flamingo Land Theme Park and 31km from Dalby Forest, offering easy access to the North York Moors National Park. It’s a peaceful retreat in a charming market town with plenty of shops, restaurants and attractions.
This comfortable property is ideal for families, with a 45 square metre floor area and a capacity of 4 guests. It has a fully equipped kitchen, a washing machine, a cosy fireplace, a private garden, and free Wi-Fi.

Best Helmsley holiday rentals with parking

Foxglove Cottage - Helmsley
8.2 9 reviews

Foxglove Cottage

house, York
Saxon House (7) - Helmsley
10 2 reviews

Saxon House (7)

apartment
Wisteria Cottage In The Heart Of Helmsley - Helmsley
9.0 1 review

Wisteria Cottage In The Heart Of Helmsley

house, Helmsley
The Coach House - Helmsley
10 3 reviews

The Coach House

house
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