Compare Vacation Rentals & Airbnb in Helmsley

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Helmsley vacation rentals
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119 Rentals and Airbnb in Helmsley

Best family friendly Helmsley vacation rentals

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

The Cake House - Helmsley
9.9 190 reviews

The Cake House

apartment
The Cake House, a Cawton, North Yorkshire holiday home, is situated a short walk from the Ebor Way, 11km from Helmsley and a 30-minute drive from York.
This single-storey dwelling sleeps eight guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen with dishwasher, secure garden, and pet-friendly features (a £25 charge per dog applies).
Apartment ∙ 2 Bedrooms ∙ 3 Guests - Helmsley
No reviews

Apartment ∙ 2 Bedrooms ∙ 3 Guests

apartment, Kirkbymoorside
This Piercy End house in Kirkbymoorside offers a convenient base for exploring the North York Moors National Park, being a 40km drive from Malton railway station with links to York, Leeds and Manchester.
The self-catering property sleeps three guests in two bedrooms, one double and one small double, and boasts a modern kitchen-diner with integrated appliances, a spacious shower room with underfloor heating, and a sheltered patio.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Helmsley
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Oswaldkirk
St Gregory's Cottage, a pet-friendly self-catering property in Oswaldkirk, North Yorkshire, is situated 6.4km from Helmsley and offers easy access to Rievaulx Abbey, Byland Abbey, Ampleforth Abbey, and Nunnington Hall.
This one-bedroom cottage sleeps two guests and features a super-king-size bed, a kitchen with fridge, microwave, and dishwasher, a garden, off-road parking, and Wi-Fi.
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.

Best Helmsley vacation rentals with a balcony

Cavendish Court - Helmsley
9.9 147 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.
Cozy Cottage Retreat Near Historic York - Helmsley
9.2 66 reviews

Cozy Cottage Retreat Near Historic York

house, York
This charming cottage is located in York, just 32 kilometres from Flamingo Land Theme Park and 38 kilometres from Dalby Forest, offering stunning views of the North York Moors. The property has received excellent user, location and cleanliness ratings.
The cottage has one bedroom and one bathroom and is 60 square metres in size. It comes with a fully equipped kitchen, a private garden, a terrace, free parking and complimentary Wi-Fi, as well as a fireplace, a jacuzzi and a microwave oven.
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.
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.

Frequently Asked Questions about vacation rentals in Helmsley

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

    Helmsley Castle is a must-see, a 12th-century fortress with stunning views. The Ryedale Folk Museum is great for learning about the local history and culture. If you're into gardens, the beautiful Helmsley Walled Garden is a treat.
  • What are the best Airbnb and vacation rentals in Helmsley?

    Bilsdale Cottage, Spacious House 3 Ensuite Bedrooms - Sleeps 6 - Centre Of Helmsley - Pet Friendly - and The Flat @ 2 Castlegate are the most popular Airbnb and vacation rentals in Helmsley among travelers.

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

    The Cleveland Way National Trail passes right through Helmsley, offering scenic views. The Helmsley to Rievaulx Abbey walk is a classic, taking you through the beautiful Rievaulx Forest. For cycling, the Helmsley to Pickering route is flat and easy, perfect for a leisurely ride.
  • What are the most popular Airbnbs in Helmsley?

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

    Helmsley is a great base for exploring the North York Moors National Park. You can go hiking, cycling, horse riding, and even try your hand at rock climbing at the nearby Sutton Bank.
  • What are the best vacation rentals with a pool in Helmsley?

    The best vacation 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 away, and you can easily reach the historic city of Pickering in around 15 minutes. The market town of Thirsk is also within easy reach, about a 20-minute drive.
  • 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 a kitchen, a living room, and a bathroom. Many also offer amenities like Wi-Fi, a washing machine, and a dryer. Some even have a garden or patio.
  • What are the best rentals or Airbnbs with a jacuzzi in Helmsley?

    The best vacation rentals or Airbnb with a jacuzzi in Helmsley are The Pheasant, The Old Bank and The Helmsley Retreat.

  • 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 pleasant and the countryside is in bloom. Autumn is also a beautiful time to visit, with the changing colours of the leaves.

Popular destinations

Best Helmsley vacation 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.

Best Helmsley vacation rentals with a fireplace

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

Holly Cottage, Pet Friendly, Character Holiday Cottage In Helmsley

cottage, York
This pet-friendly holiday cottage is situated in the York district, a 4-minute drive from the North York Moors National Park and 5 minutes from Duncombe Park.
This 130 square meter holiday home accommodates up to six guests across three bedrooms and three bathrooms, featuring a well-equipped kitchen, Wi-Fi, a television, and a washing machine, with opportunities for cycling and fishing nearby.
Ford End Cottage, Ampleforth - Helmsley
No reviews

Ford End Cottage, Ampleforth

cottage, York
This converted carriage shed, offering accommodation for six guests, is situated in Ampleforth, North Yorkshire, within the North York Moors National Park, just 4 kilometers from the market town of Helmsley.
The property features three bedrooms, including a king-size with an en-suite, a sitting room with a woodburning stove, and an enclosed patio, with pets welcome and the North York Moors National Park ideal for walking and cycling nearby.
2 Bed In Helmsley (Oc-g0037) - Helmsley
No reviews

2 Bed In Helmsley (Oc-g0037)

cottage, Helmsley
This two-bedroom holiday let in Helmsley is located within easy reach of the village's independent shops, cafes, and dining, and is situated just 800 metres from Helmsley Castle and a short walk from Helmsley Walled Garden, offering convenient access to the North York Moors National Park. This property accommodates up to three guests and features a wood burner, Wi-Fi, a well-equipped kitchen with a dishwasher, and two garden areas, including a patio with a BBQ, with off-road parking for one vehicle provided.
The Byre - Stone Cottage In The Heart Of Helmsley - Helmsley
8.5 2 reviews

The Byre - Stone Cottage In The Heart Of Helmsley

house, Helmsley
This stone cottage in Helmsley is situated 24 kilometres from York Minster and York Train Station, and 24 kilometres from Flamingo Land Theme Park.
This 60 square meter property accommodates two guests with one bedroom, one bathroom, a kitchen with a fridge, microwave oven, and dishwasher, free WiFi, free parking, and an outdoor dining area.
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