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.

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.
Host & Stay - Willow Cottage - Helmsley
9.3 165 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.
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.
Campion Cabin - Helmsley
No reviews

Campion Cabin

cabin, Helmsley
Campion Cabin is located in Helmsley, 55 kilometers from Teesside International Airport, offering a secluded retreat near Helmsley Castle and Rievaulx Abbey.
This 30 square meter log cabin accommodates two guests and features a private entrance, a fully equipped kitchen, a hot tub, and a sun terrace, with barbecue facilities and outdoor seating for al fresco dining.

Best family friendly Helmsley holiday rentals

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

4 Bed In Rosedale Abbey (Oc-g0074) - Helmsley
No reviews

4 Bed In Rosedale Abbey (Oc-g0074)

apartment
This secluded four-bedroom apartment is situated near Rosedale East within the North York Moors National Park, offering a tranquil retreat 3 kilometres north of Blakey Ridge and 1 kilometre from the village of Rosedale Abbey.
This spacious four-bedroom, four-bathroom flat accommodates up to eight guests and features a dishwasher, jacuzzi, and garden, with access to walking and cycling trails ideal for exploring the surrounding ancient woodland and valleys.
Fairfax Cottage - (See Also Cholmeley Cottage) - Helmsley
10 95 reviews

Fairfax Cottage - (See Also Cholmeley Cottage)

apartment
This charming cottage is located in the Howardian Hills AONB, just 20 kilometers from York and within easy reach of the Yorkshire Moors, Dales and coast. It has consistently received excellent user ratings for location, cleanliness and overall experience.
The cottage is a comfortable and spacious property with three bedrooms, sleeping up to five guests. It has a well-equipped kitchen, a private garden with a patio, and parking for two cars. Guests can enjoy a range of activities in the surrounding area, including walking, cycling and exploring nearby attractions.
Lily Pad - Uk49104 - Helmsley
10 12 reviews

Lily Pad - Uk49104

apartment
Lily Pad Cottage, a two-bedroom Helmsley holiday home, is located a minute's walk from Helmsley town centre, close to Helmsley Castle and Helmsley Walled Garden.
This self-catering property sleeps four guests and features a fully equipped kitchen/diner with dishwasher and washer-dryer, a wood-burning stove, Smart TVs in both bedrooms, a private patio, and private parking for one car; travel cot and highchair are provided.
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.

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

Honeysuckle Cottage - Helmsley
9.6 106 reviews

Honeysuckle Cottage

apartment
This charming holiday home is situated in the centre of Helmsley, just a short walk from the historic Helmsley Castle and the picturesque Helmsley Walled Garden. The property has received excellent ratings for its cleanliness, location and overall experience from previous guests.
The accommodation offers a comfortable and peaceful retreat for up to four guests. It features a well-equipped kitchen with a fridge, freezer, microwave oven and dishwasher, along with a garden for relaxing and enjoying the fresh air.
Cottage ∙ 3 Bedrooms ∙ 4 Guests - Helmsley
9.8 6 reviews

Cottage ∙ 3 Bedrooms ∙ 4 Guests

cottage, Helmsley
This Helmsley cottage is situated 0.3km from Helmsley's market square and 1.6km from Duncombe Park, offering easy access to the Cleveland Way and Ebor Way walking and cycling routes.
The 45 square metre property sleeps up to five (including one child over 5), features three bedrooms, one bathroom, a fully equipped kitchen (excluding a washing machine), and a south-facing courtyard garden; pets are welcome.
Wisteria Cottage & Barn - Sleeping 10 - Helmsley
No reviews

Wisteria Cottage & Barn - Sleeping 10

apartment
This Wisteria Cottage, a five-bedroom holiday home, is centrally located in Helmsley market town, within the North York Moors National Park, offering a quiet position with private parking and garden.
This property accommodates up to 10 guests with a spacious kitchen, a sitting room with an open fire, a private patio, and is within easy reach of the North Yorkshire countryside for walks.
3 Bedroom Accommodation In Helmsley - Helmsley
No reviews

3 Bedroom Accommodation In Helmsley

cottage, Helmsley
This three-bedroom Helmsley holiday home is situated a five-minute walk from the North York Moors National Park and the Cleveland Way, offering easy access to Helmsley Arts Centre and Nunnington Hall.
Sleeping six guests, the property boasts three bathrooms, a fully equipped kitchen with a dishwasher, free Wi-Fi, laundry facilities, a fireplace and central heating; pets are welcome.

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.

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

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.

2 Bed In Helmsley (Oc-g0037) - Helmsley
No reviews

2 Bed In Helmsley (Oc-g0037)

cottage, Helmsley
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Helmsley
9.0 7 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Helmsley
Host & Stay | Croft Cottage - Helmsley
10 14 reviews

Host & Stay | Croft Cottage

apartment
Foxglove Cottage, Harome - Helmsley
No reviews

Foxglove Cottage, Harome

apartment, York

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.

Fox Cover Cottage - Helmsley
9.9 16 reviews

Fox Cover Cottage

apartment

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.

The Old Bank Apartments - Helmsley
No reviews

The Old Bank Apartments

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

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

apartment
Waters Edge Cabin - Helmsley
No reviews

Waters Edge Cabin

cabin, Helmsley
The Coppice Cabin @ Helmsley Meadows - Helmsley
10 6 reviews

The Coppice Cabin @ Helmsley Meadows

cabin
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