Holiday Rentals in Helmsley

119 available vacation rental offers

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Helmsley holiday rentals
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Best Holiday rentals and Airbnb offers in Helmsley

Guest-Favourite Self-Catering Rentals with a Balcony in Helmsley

Morning coffee with views across the hills is a simple pleasure in these holiday rentals in Helmsley. Each option features a beautiful outlook.

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.
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.
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.
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.

Best family friendly Helmsley holiday rentals

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

The Coach House - Helmsley
10 4 reviews

The Coach House

house
The Coach House, a self-catering property in Bilsdale, North Yorkshire, is situated six miles (approximately 9.6km) north of Helmsley, within the North Yorkshire Moors National Park.
This two-bedroom dwelling, sleeping up to four guests, offers an open-plan kitchen/living area, a garden, parking, and access to Freeview TV and streaming services; breakfast and dinner hampers are available upon pre-booking.
31 Bridge Street - Helmsley
9.8 174 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.
The Old Cart House - Helmsley
9.7 16 reviews

The Old Cart House

house, Salton
The Old Cart House is situated in the Ryedale district, just 5.2 kilometres from Castle Howard, a magnificent stately home, and a short drive from the market towns of Malton, Pickering, Helmsley, and Kirkbymoorside. The property has received excellent ratings for its location, cleanliness, and overall experience, providing a peaceful escape in the Yorkshire countryside.
This two-bedroom home offers 140 square metres of space, featuring a fully equipped kitchen, a garden with barbecue facilities, and a tennis court. Guests can enjoy free parking, Wi-Fi, and a range of services including grocery delivery, making it an ideal base for exploring the area's cycling and hiking trails.
3 Bed In Cawton (Oc-t32407) - Helmsley
No reviews

3 Bed In Cawton (Oc-t32407)

cottage, Cawton
This rural country cottage in Cawton, North Yorkshire, is located on the edge of the Howardian Hills National Landscape, 5.6 kilometres from Hovingham and 11.2 kilometres from Helmsley, offering a prime position for walkers with the Ebor Way passing through the village and close proximity to the North York Moors Cycleway.
This family-friendly holiday home accommodates six guests in three bedrooms and two bathrooms, featuring a well-equipped kitchen with a microwave oven, a lounge/diner with a wood burner, an enclosed patio with outdoor furniture and a fire pit, and a garage with a pool table and tumble dryer.

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 castle with impressive ruins. The Ryedale Folk Museum is great for learning about the local history and there's the beautiful Helmsley Walled Garden with its stunning displays.
  • 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 fantastic views. The 10-mile Helmsley to Rievaulx Abbey cycle route is popular and the 6.5-mile Helmsley Circular Walk is great for a shorter stroll.
  • What are the most popular Airbnbs in Helmsley?

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

    You can go fishing at the River Rye, there's a golf course at Helmsley, and you can go horse riding at one of the local riding schools. The area is also great for birdwatching.
  • 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?

    You can easily get to York, which is about 40km away, and the historic city of Whitby is about 60km away. The market town of Pickering is only 10km away and is worth a visit.
  • 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 kitchens, bathrooms, and living areas. Many will also have Wi-Fi, TVs, and washing machines. Some may have gardens or patios too.
  • 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 is during the spring or summer months when the weather is warmer and the days are longer. Autumn is also beautiful with the changing colours of the leaves.
  • What are the local dishes in Helmsley region?

    You should try the Yorkshire Pudding, a traditional dish made with batter and served with roast beef. The local cheeses are also delicious, especially Wensleydale cheese.

Popular destinations

Best Helmsley holiday rentals with a fireplace

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.
Hideaway Cottage - Helmsley
8.3 12 reviews

Hideaway Cottage

apartment
Hideaway Cottage is a two-bedroom holiday let located in Ampleforth village, 31 kilometres from the historical city of York.
This pet-friendly cottage accommodates four guests and features a well-equipped kitchen with a dishwasher, a living room with a log burner, and a private terraced garden with direct access to walking trails.
Bellwether - Helmsley
9.9 98 reviews

Bellwether

house, York
This Bellwether cottage is a peaceful countryside retreat near Flamingo Land Theme Park, approximately 21 kilometres from the park and 40 kilometres from York city centre.
The 90 square metre property offers one bedroom, one bathroom, a fully equipped kitchen with fridge and microwave, free Wi-Fi, a cosy fireplace, private garden, parking, and is perfect for couples or solo travellers seeking self-catering accommodation near Dalby Forest.
3 Bed In Ampleforth (Oc-m34673) - Helmsley
No reviews

3 Bed In Ampleforth (Oc-m34673)

cottage, Ampleforth
This Ampleforth holiday home is situated 3 kilometres by car from Ampleforth Abbey and 4 kilometres by car from Byland Abbey, offering convenient access to historic sites.
This 3-bedroom, 2-bathroom cottage accommodates up to 6 guests and features a fully equipped kitchen with a microwave oven and dishwasher, complimentary Wi-Fi, a garden, barbecue facilities, and on-site parking.

Neighborhoods and points of interest in Helmsley

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.

Top-Rated 5-Star Self-Catering Holiday Rentals in Helmsley

A mountain luxury holiday rental or Airbnb in Helmsley sets the right tone from the moment you arrive with 5-star comfort. Explore our top-rated stays.

Wisteria Cottage & Barn - Sleeps 10 And Welcomes Dogs - Helmsley
No reviews

Wisteria Cottage & Barn - Sleeps 10 And Welcomes Dogs

house, Helmsley

Find the Best Pet-Friendly Holiday Rentals in Helmsley

No need to leave the dog behind in Helmsley. These holiday rentals offer dog-friendly trails and plenty of space to roam. Start planning now.

Easy Stroll To Pubs, Shops And Cafés - Helmsley
9.9 38 reviews

Easy Stroll To Pubs, Shops And Cafés

apartment
Cliff Stud Retreat, Helmsley - Cecil Cottage - Helmsley
9.7 154 reviews

Cliff Stud Retreat, Helmsley - Cecil Cottage

apartment
The Old Hayloft - Helmsley
No reviews

The Old Hayloft

apartment
Appartement-prestige-sdb Privée Avec Douche-vue Su - Helmsley
No reviews

Appartement-prestige-sdb Privée Avec Douche-vue Su

apartment

Handpicked Self-Catering Rentals with a Pool in Helmsley

These holiday rentals in the hills around Helmsley include a pool, so a refreshing dip after a long walk is always an option.

Cliff House - Helmsley
9.4 19 reviews

Cliff House

house, York
St Gregorys Cottage, Pet Friendly, With A Garden In Helmsley - Helmsley
No reviews

St Gregorys Cottage, Pet Friendly, With A Garden In Helmsley

cottage, York

Choose the Right Holiday Rentals with a Hot Tub in Helmsley

Coming back to a hot tub after a day in the hills changes the whole feel of a stay. These holiday rentals in Helmsley are ready for you.

Eisa Yurt - Helmsley
9.8 73 reviews

Eisa Yurt

glamping, York
Campion Cabin @ Helmsley Meadows - Helmsley
10 7 reviews

Campion Cabin @ Helmsley Meadows

cabin
Prestige-appartement-sdb Privée-vue Sur Rue-sleeps - Helmsley
No reviews

Prestige-appartement-sdb Privée-vue Sur Rue-sleeps

apartment
Crossing Cottage - Helmsley
9.9 28 reviews

Crossing Cottage

house, Helmsley
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