Find short term rentals in Helmsley at the best prices

The Fairfax Arms, a guest house in Gilling East, North Yorkshire, enjoys a rural setting approximately 48km from York and on the edge of the North York Moors National Park.
This B&B offers a twin room in its main building, featuring en-suite facilities, modern furnishings, and some rooms with exposed beams, accommodating up to two guests and providing on-site dining.

This Helmsley cottage is centrally located in the market town, within easy walking distance of Helmsley Castle and a short drive (approximately 20 km) from the North York Moors National Park.
This three-bedroom property sleeps five, offering an open-plan living space, a modern kitchen with dishwasher, a private garden with barbecue, and private parking for two cars; highchair and cot are available.

This duplex apartment is centrally located in Helmsley, a market town within the North York Moors National Park, directly overlooking the historic market square.
Offering accommodation for up to 4 guests, this family-friendly property features 2 bedrooms, 2 bathrooms, a Jacuzzi, garden, parking, and a high-end kitchen with Miele appliances, all within a stunning historic conversion of the town's old bank.

This Ampleforth village flat offers a peaceful base, situated approximately 6.5 kilometres from Helmsley and close to Ampleforth Abbey and the North York Moors National Park.
This family-friendly property accommodates up to five guests with three bedrooms, one bathroom, a fully equipped kitchen/dining room, a cosy living room with a woodburner, a private garden, and includes a travel cot and highchair.

Plumpton Court is a charming bed and breakfast located in the village of Nawton, just 7km from the market town of Thirsk and the Yorkshire Dales. It has received excellent ratings for its location, cleanliness, and overall experience.
This historic 17th-century property offers contemporary comfort with modern amenities. Guests can enjoy a relaxing atmosphere, a cosy bar, delicious breakfasts with locally sourced ingredients, and a garden with a terrace.

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.

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.

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.

This adults-only retreat is situated in Helmsley Meadows, offering countryside and pond views, with a 2.4-kilometre walk to Helmsley town and under 2.4 kilometres to The Star Inn at Harome.
This one-bedroom lodge provides a private decking area with a wood-fired hot tub and BBQ firepit, a kitchen equipped with a fridge and microwave, and direct access to 6 acres of meadows, ideal for exploring.

This cottage offers a peaceful rural retreat on the outskirts of Gillamoor, located 4 kilometres from Kirkbymoorside, 13 kilometres from Helmsley, and 16 kilometres from Pickering, with direct access to the North York Moors National Park.
This one-bedroom holiday home accommodates two guests, featuring a super king-size bed, a wood burner, a kitchen, a patio garden, and off-road parking, making it ideal for couples exploring the North York Moors.

Saxon House, in the North Yorkshire village of Harome, is ideally located next to The Pheasant and The Star Inn, two Michelin-starred restaurants.
This five-bedroom house, sleeping nine, boasts a spacious open-plan kitchen/dining area, a triple-aspect sitting room with a wood-burning stove, a generous enclosed garden, and ample parking, plus an annexe available for larger groups; a highchair and travel cot are provided (linen not included).

This Gilling East cottage is situated in the Howardian Hills Area of Outstanding Natural Beauty, 6 kilometres from Helmsley and 18 kilometres from Pickering, providing access to the North York Moors National Park and the North Yorkshire Heritage Coast.
This 2-bedroom, 1-bathroom holiday home accommodates up to 3 guests, featuring an open-plan living space with underfloor heating, a kitchen with a dishwasher, and a shared tennis court, with off-road parking for one car and a patio with seating.

This Kirkbymoorside cottage, centrally located within walking distance of shops, pubs, and cafes, offers easy access to the North Yorkshire Moors National Park (a short drive away).
Sleeping four, this self-catering property features two bedrooms, one bathroom, a well-equipped kitchen with appliances including a fridge-freezer and washing machine, plus off-street parking and a small yard with seating.

This stone-built cottage is located in Helmsley, North Yorkshire, within 500 meters of the market square and its independent shops and eateries, offering easy access to Helmsley Castle and the North York Moors.
This pet-friendly, family-friendly holiday let accommodates three guests in two bedrooms, features a well-equipped kitchen with a dishwasher, and includes a private rear garden for relaxation.

This detached cottage is located in Upper Ryedale, a short walk from Helmsley's market town amenities and within 1.6 kilometers of Helmsley Castle and the National Birds of Prey Centre.
Sleeping up to six guests, this luxurious property offers three bedrooms, including underfloor heating, a Smart TV, a well-equipped kitchen with a wine cooler and coffee machine, and an enclosed garden with private parking for three cars and an EV charger.

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.