Holiday Rentals in Helmsley

119 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Helmsley holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

2 Bed In York (Oc-81052) - Helmsley
No reviews

2 Bed In York (Oc-81052)

apartment
This Helmsley apartment, ideally located within a 5-minute walk of Helmsley Castle and the town centre's pubs and shops, offers easy access to the North Yorkshire Moors National Park.
The self-catering property sleeps up to four guests in two bedrooms, boasts an enclosed private garden, allocated parking, a well-equipped kitchen with a dishwasher, and a family bathroom with a separate WC.
Cottage ∙ 2 Bedrooms ∙ 2 Guests - Helmsley
9.8 10 reviews

Cottage ∙ 2 Bedrooms ∙ 2 Guests

cottage, Nawton
This Nawton stone cottage, in North Yorkshire, is situated approximately 15.3 km from Byland Abbey and 17.7 km from the Sutton Bank National Park Centre.
The two-bedroom property, sleeping up to three guests, offers a family shower room, country-style kitchen with dishwasher, garden with BBQ, off-street parking for a small car, and is close to Yorkshire Lavender Farm.
Cottage ∙ 5 Bedrooms ∙ 8 Guests - Helmsley
No reviews

Cottage ∙ 5 Bedrooms ∙ 8 Guests

cottage
This stone barn conversion, Cockpit, is located in the North Yorkshire village of Cawton, 11 kilometers from the market town of Helmsley and within 32 kilometers of York and Flamingo Land.
This 5-bedroom holiday home accommodates up to 8 guests and offers a large living area, a snug with a wood burner, two patio areas with outdoor furniture and a fire pit, a well-equipped kitchen, and parking for three cars, situated in a peaceful, rural setting alongside a working farm ideal for exploring the Ebor Way walking trails.
Silent Springs - Helmsley
10 3 reviews

Silent Springs

apartment
Silent Springs cottage, a one-bedroom property in Nawton, near Helmsley, North Yorkshire, offers easy access to the North York Moors National Park and is a short drive (approximately 6km) from the historic market town of Helmsley.
This pet-friendly holiday home sleeps four, featuring a cosy open-plan layout with a king-size bed and double sofa bed, a fully equipped kitchen with dishwasher, private patio with barbecue, and on-site parking for two cars; travel cot and highchair available on request.

Best Helmsley holiday rentals with a balcony

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.
Rye Court Cottage - Stunning Cottage In Central Helmsley With Parking - Helmsley
8.9 178 reviews

Rye Court Cottage - Stunning Cottage In Central Helmsley With Parking

house, Helmsley
Rye Court Cottage is a centrally located house in Helmsley, just 15 miles from Flamingo Land Theme Park and 19 miles from Dalby Forest, making it an ideal base for exploring the Yorkshire countryside. This property has received excellent ratings for location, cleanliness, and overall user experience.
The house has 3 bedrooms and 2 bathrooms, comfortably accommodating families or groups of friends. Amenities include a fully equipped kitchen with a dishwasher, a washing machine, a fireplace for cosy evenings, free Wi-Fi, and secure bicycle parking, perfect for exploring the surrounding area.
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 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

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.
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).
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.
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.
©2026 cozycozy.com