Find short term rentals in Helmsley at the best prices

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 stone barn conversion, offering accommodation for eight guests, is located in Cawton, North Yorkshire, 11 kilometres from Helmsley and within 32 kilometres of York, Nunnington Hall, and Flamingo Land.
This detached cottage features a spacious living area, a separate snug with a wood burner, a well-equipped kitchen, and an enclosed garden with outdoor furniture, a fire pit, and a charcoal barbecue, alongside private parking for three cars.

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.

This Grade II listed Georgian cottage in Hovingham, York, offers a prime location directly opposite the village bakery, within easy walking distance of local amenities including traditional pubs, a Michelin-starred restaurant, and just minutes from Castle Howard estate.
Spanning 174 square meters, this four-bedroom property accommodates up to seven guests and features generous living spaces with a wood-burning stove, a thoughtfully designed kitchen, a main bathroom with a roll-top bath and rainfall shower, and an enclosed garden, with internet provided.

Shallowdale House is a charming bed and breakfast located 8 kilometres from Helmsley, nestled on the southern edge of the North York Moors National Park, offering stunning views of the Howardian Hills. This award-winning property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The guest house offers spacious and elegant rooms, each with a unique design and modern amenities. Enjoy the on-site restaurant, the comfortable drawing room, the first-floor library, and the beautiful gardens with a terrace, all while taking advantage of the free Wi-Fi and parking.

Wisteria Cottage is a stone holiday home centrally located in Helmsley, within the North York Moors National Park, offering a quiet position 200 meters from the market town centre with private gated parking and a garden.
This four-bedroom cottage sleeps up to eight guests and features elegant furnishings, an open fire, a well-equipped kitchen with a range cooker, a private patio with seating, and welcomes pets.

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.

This Helmsley first-floor flat, situated above an art gallery and overlooking Helmsley Castle, offers stunning views and is within easy walking distance of the town's cafes, restaurants, and shops.
The one-bedroom apartment, sleeping two guests, features a spacious sitting room, kitchen-diner, and bathroom with shower, plus private garden access and convenient on-street parking despite nearby building works.

This unique barn conversion is located 5.6 kilometres south of Kirkbymoorside, offering convenient access to the North York Moors National Park and within driving distance of Pickering and York.
This property features three bedrooms accommodating up to six guests, with an open-plan living area, en-suite facilities, off-road parking, and is pet-friendly, providing internet access.

Clematis Cottage, a pet-friendly holiday home in Gilling East, North Yorkshire, is situated in the Howardian Hills Area of Outstanding Natural Beauty, 8km from Helmsley and a short drive from York.
This one-bedroom self-catering property sleeps two, boasts a well-equipped kitchen including a dishwasher, offers off-road parking, and provides access to a shared tennis court.

This Ampleforth holiday cottage is situated in York, a 2-minute drive from St. Lawrence Abbey and 4 minutes from the Howardian Hills.
This family-friendly lodge accommodates four guests across two bedrooms and one bathroom, offering a fully equipped kitchen with a microwave and dishwasher, complimentary Wi-Fi, and proximity to Ampleforth College Golf Club and the North York Moors National Park.

This rural retreat, a cottage in Cawton, North Yorkshire, is situated on the edge of the Howardian Hills National Landscape, offering 5.6 kilometres to Hovingham and 11.2 kilometres to Helmsley's shops, eateries, and castle.
This family-friendly property accommodates six guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen, a lounge with a wood burner, an enclosed garden with a fire pit, and a garage with a pool table and tumble dryer, making it ideal for walkers and cyclists exploring the Ebor Way and North York Moors Cycleway.