Holiday Rentals in Helmsley

119 available vacation rental offers

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Helmsley holiday rentals
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119 Holiday Rentals and Airbnb in Helmsley

Best family friendly Helmsley holiday rentals

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

Clematis Cottage @ Coach House Cott - Helmsley
9.8 49 reviews

Clematis Cottage @ Coach House Cott

apartment
Clematis Cottage is located near the charming market town of Helmsley, close to the North Yorkshire Moors and the city of York, making it an ideal base for exploring the region. The cottage has received excellent ratings for its cleanliness, location and overall experience.
This one-bedroom holiday home is perfect for a couple or a small family. Clematis Cottage offers a range of amenities, including a modern kitchen, a shared laundry area, a tennis court, a BBQ, a large garden, and free Wi-Fi.
Helmsley Cottage - Helmsley
No reviews

Helmsley Cottage

apartment
This three-bedroom holiday cottage in Helmsley, North Yorkshire, offers a prime position within the village, serving as a gateway to the North York Moors National Park, with the park entrance approximately 1 kilometre away.
Accommodating up to six guests, this pet-friendly property features a kitchen with a fridge, microwave, and dishwasher, and is an ideal base for exploring the surrounding landscapes, with local amenities within 500 meters.
60 M² Cottage ∙ 1 Bedroom ∙ 3 Guests - Helmsley
9.2 79 reviews

60 M² Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage
Brackensyke cottage, a self-catering holiday home in Ampleforth, North Yorkshire, is situated a 40km drive from York, offering easy access to its historical attractions.
This one-bedroom property boasts 60 square metres of living space, sleeping up to three guests, and includes a well-equipped kitchen, a private garden, on-site parking, and amenities such as a multi-fuel stove, smart TV, and Wi-Fi.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Helmsley
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Silent Springs cottage, a self-catering property in Nawton near Helmsley, North Yorkshire, is a short distance from Helmsley's historic town centre and picturesque walking trails in the North Yorkshire Moors National Park.
This one-bedroom holiday home offers a cosy open-plan layout sleeping four, featuring a king-size bed (with twin option), a double sofa bed, a fully equipped kitchen with dishwasher, a private patio with barbecue, and is close to the North Yorkshire Moors Railway in Pickering and the Yorkshire Coast.

Best Helmsley holiday rentals with a balcony

The Old School House - Helmsley
9.5 2 reviews

The Old School House

house, Lastingham
The Old School House, a family-friendly holiday home in Lastingham, is situated 17.7 kilometres from Flamingo Land Theme Park and 20.9 kilometres from Dalby Forest.
This spacious 400 square meter property accommodates up to 15 guests, offering a fully equipped kitchen with a dishwasher and oven, free WiFi, and garden access, with cycling and hiking opportunities nearby.
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.
Fairview, Ampleforth, North York Moors - Helmsley
No reviews

Fairview, Ampleforth, North York Moors

apartment, Ampleforth
This Ampleforth holiday home is situated 1.1km from Ampleforth Abbey, offering easy access to Ampleforth College Golf Club and the Howardian Hills within a 5km radius.
The 1 square metre property sleeps 3 guests and includes 2 bedrooms, 1 bathroom, a fully equipped kitchen with fridge, microwave, and dishwasher, plus a garden, terrace, parking and in-house laundry facilities.
Waters Edge Cabin - Helmsley
10 1 review

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 Norman castle with a rich history. You can also visit the Ryedale Folk Museum, which showcases the region's heritage. For a scenic walk, head to the beautiful Rievaulx Abbey ruins.
  • 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 stunning views. For a shorter walk, try the Helmsley Walled Garden, it's a beautiful place to stroll. For cycling, the scenic route along the River Rye is popular.
  • What are the most popular Airbnbs in Helmsley?

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

    Helmsley is a great spot for walking, cycling, and horse riding. You can also go fishing in the River Rye or try your hand at archery at the Helmsley Archery Club.
  • 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 40-minute drive from Helmsley and is a popular day trip. You can also easily visit Pickering, which is known for its steam railway, and Whitby, a coastal town famous for its abbey and fish and chips.
  • 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 have kitchens, living rooms, and bedrooms. Many also offer amenities like Wi-Fi, laundry facilities, and parking.
  • 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?

    Helmsley is beautiful all year round, but it's especially lovely in spring and summer when the gardens are in bloom. Autumn is also a great time to visit for the changing colours of the leaves.
  • What are the local dishes in Helmsley region?

    The Yorkshire Dales are known for their hearty food. Try a traditional Yorkshire pudding with roast beef, or a hearty pie made with local ingredients. You can also find delicious cheeses and local beers in the area.

Popular destinations

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.

Best Helmsley holiday rentals with a fireplace

Mole End - Helmsley
No reviews

Mole End

cottage, Wass
Mole End is a secluded single-storey annexe located within the North York Moors National Park, approximately 3.2 kilometers from Helmsley and a short drive from Rievaulx Abbey.
This 80 square meter cottage offers accommodation for two, featuring one bedroom and one bathroom, with a well-equipped kitchen, a log burner, and a peaceful garden with outdoor furniture, all set within 45 acres of woodland and pasture.
Ryegate Cottage - Helmsley
8.0 1 review

Ryegate Cottage

apartment
This two-bedroom flat in Helmsley is centrally located, offering easy walking access to independent shops, pubs, tea rooms, restaurants, Helmsley Castle, the Walled Garden, and Duncombe Park, with the North Yorkshire Moors National Park a short distance away.
This pet-friendly apartment accommodates up to four guests and features a well-equipped kitchen with a Rangemaster cooker, a living room with an open fireplace, two bathrooms including an en suite, and a spacious garden with a patio and lawn, with Wi-Fi, linen, towels, and initial fuel for the fire provided.
Meadow Cottage On Working Farm - Helmsley
No reviews

Meadow Cottage On Working Farm

cottage, York
This barn conversion is situated near Kirkbymoorside in North Yorkshire, offering straightforward access to the North York Moors National Park and lying within a 50-kilometre drive of York.
This two-bedroom cottage accommodates four guests and features an open-plan living area with a woodburning stove, off-road parking, and a private courtyard, making it an ideal base for exploring the surrounding countryside and attractions such as Flamingo Land.
Host & Stay - Willow Cottage - Helmsley
9.2 169 reviews

Host & Stay - Willow Cottage

house, Helmsley
Willow Cottage is a charming house located in Helmsley, a market town in the North York Moors National Park, just 30km from Dalby Forest and 39km from York Minster. The property has received excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The 69 square metre house has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a patio and garden, as well as free Wi-Fi, a washing machine and a flat-screen TV.
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