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

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Helmsley
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Helmsley
Ryegate Cottage is a two-bedroom holiday home situated in Helmsley, Ryegate, just 500 meters from Helmsley Castle and the walled garden, and within easy reach of the North Yorkshire Moors National Park. This pet-friendly accommodation for four guests features a well-equipped kitchen with a Rangemaster cooker, a living room with an open fireplace, and a back garden with a patio, offering convenient access to local shops and restaurants.
The Cottage Gillamoor - Helmsley
9.5 63 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.
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).
Kirby Cottage - Helmsley
9.8 10 reviews

Kirby Cottage

house, Harome
Kirby Cottage is located in the village of Harome, just 21km from Flamingo Land Theme Park and 29km from Dalby Forest. The cottage has received excellent ratings for location, cleanliness, and overall experience.
This 2-bedroom property sleeps up to 4 guests and offers a comfortable and convenient stay. The cottage features a fully equipped kitchen, a garden, and free Wi-Fi, making it ideal for families and groups looking for a peaceful escape.

Best Helmsley holiday rentals with a balcony

Host & Stay - Willow Cottage - Helmsley
9.2 165 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.
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.
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.
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.

Frequently asked questions about holiday rentals in Helmsley

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

    Helmsley is a great place for outdoor activities. You can go horse riding, fishing, or play golf at the local course. There are also plenty of opportunities for walking, cycling, and birdwatching in the surrounding countryside. The North York Moors National Park is just a short drive away and offers a wide range of outdoor activities.
  • What are the best Airbnb and holiday rentals in Helmsley?

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

    York is about an hour's drive away, and offers a wealth of historical attractions. The coastal town of Whitby is also easily accessible, with its iconic abbey and charming harbour. For a more rural experience, visit the market town of Pickering, known for its steam railway and the North York Moors Railway.
  • What are the most popular Airbnbs in Helmsley?

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

    Most vacation rentals in Helmsley offer basic amenities such as a kitchen, bathroom, and comfortable beds. Many also have a garden or patio, and some even have hot tubs or swimming pools. It's worth checking the listing carefully to see what amenities are included.
  • 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 time of year is best to rent a vacation rental Helmsley?

    Spring and autumn are lovely times to visit Helmsley, when the weather is mild and the crowds are smaller. Summer is a popular time to visit, but it can get busy. If you're looking for a more peaceful experience, consider visiting in the winter months, when the landscape is covered in snow.
  • What are the best rentals for families and kids in Helmsley?

  • 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, Crossing Cottage and The Old Bank.

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

Cottage ∙ 2 Bedrooms ∙ 3 Guests - Helmsley
8.6 8 reviews

Cottage ∙ 2 Bedrooms ∙ 3 Guests

cottage, Helmsley
This Helmsley holiday home, a semi-detached cottage, is situated in the North York Moors National Park, less than 1.6km from Helmsley Castle and Helmsley Walled Garden, and 2.4km from Duncombe Park.
The 45 square metre property features two bedrooms (king-size with walk-in wardrobe and a single), a wet room, open-plan living space with a wood-burning stove, a fully equipped kitchen with fridge and dishwasher, and accommodates up to three guests, offering a welcome hamper upon arrival.
Robins Cottage - Helmsley
10 5 reviews

Robins Cottage

house, York
Robins Cottage, a two-bedroom house near York, is situated approximately 30 kilometres from York Minster and 32 kilometres from York Train Station, offering a peaceful retreat for families or couples.
This 150 square metre property features a spacious layout with a living room, TV, two bathrooms, an outdoor dining area, a fireplace, free Wi-Fi, and accommodates up to seven guests.
Lily Pad - Uk49104 - Helmsley
9.8 10 reviews

Lily Pad - Uk49104

house, Helmsley
Lily Pad - Uk49104, a two-bedroom house in Helmsley, North Yorkshire, is situated 24km from York and offers easy access to Flamingo Land (24km) and Dalby Forest (34km).
This self-catering property sleeps seven, features a dishwasher, free Wi-Fi, private parking, a garden, and a cosy fireplace.
31 Bridge Street - Helmsley
9.8 176 reviews

31 Bridge Street

apartment
This charming 18th-century cottage is located on Bridge Street in Helmsley, just a short walk from the market square and within easy reach of the stunning Duncombe Park estate. The cottage has received excellent user, location, and cleanliness ratings, making it a popular choice for visitors to the area.
The cottage comfortably sleeps six people across three bedrooms and two bathrooms. Guests can enjoy a well-equipped kitchen with an AGA Masterchef, a spacious conservatory, a private garden, and a range of amenities, including two log burners, two flat-screen TVs, a washing machine, and Wi-Fi.
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