Search All Cottages in Helmsley

56 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Helmsley cottages
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

56 Cottages at the best price in Helmsley

Best family friendly Helmsley cottages

Among the 56 accommodations in Helmsley, here are the 3 best family friendly cottages

4 Bed In Helmsley (Oc-l29736) - Helmsley
No reviews

4 Bed In Helmsley (Oc-l29736)

cottage, Helmsley
This stone lodge is situated in Helmsley, 800 meters from Helmsley Castle and close to the North York Moors National Park.
This property offers accommodation for eight guests with four bedrooms, four bathrooms, a sleek kitchen with a microwave oven, and private parking for two cars, ideal for families and pet owners exploring the local area.
2 Bed In York (Oc-81052) - Helmsley
No reviews

2 Bed In York (Oc-81052)

cottage, Helmsley
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.
Ford End Cottage, Ampleforth - Helmsley
No reviews

Ford End Cottage, Ampleforth

cottage, York
This converted carriage shed, offering accommodation for six guests, is situated in Ampleforth, North Yorkshire, within the North York Moors National Park, just 4 kilometers from the market town of Helmsley.
The property features three bedrooms, including a king-size with an en-suite, a sitting room with a woodburning stove, and an enclosed patio, with pets welcome and the North York Moors National Park ideal for walking and cycling nearby.

Best Helmsley cottages with a garden

3 Bed In Kirkbymoorside (Oc-g0001) - Helmsley
No reviews

3 Bed In Kirkbymoorside (Oc-g0001)

cottage, Kirkbymoorside
This detached cottage near Kirkbymoorside offers countryside views of the North York Moors, with walking paths and the town's gallery, antique shops, and market within 1.6 kilometers.
This opulent property accommodates six guests across three en-suite bedrooms, featuring a galley kitchen with a dishwasher, a private garden with a hot tub, and shared facilities including a tennis court and billiards room.
Isca Lodge - With Decking, Pet Friendly, With A Garden In Wombleton - Helmsley
No reviews

Isca Lodge - With Decking, Pet Friendly, With A Garden In Wombleton

cottage, York
This Wombleton holiday cottage is located in the Ryedale district, on the edge of the North York Moors National Park, offering access to historic York, Castle Howard, Nunnington Hall, and Rievaulx Abbey, with Helmsley and Kirkbymoorside just 4.8 kilometres away.
This 130 square meter lodge accommodates six guests in three bedrooms, including a double with an en-suite, and features a well-equipped open-plan living space with WiFi, a dishwasher, and private decking for outdoor relaxation, with pets welcome.
29 Bondgate - Helmsley
No reviews

29 Bondgate

cottage, York
This pet-friendly cottage near Helmsley, North Yorkshire, is less than 0.8km from the North York Moors National Park and Helmsley Arts Centre, and under 1.6km from Duncombe Park and the Cleveland Way.
The self-catering property offers free Wi-Fi, parking, a dishwasher, and a garden; nearby activities include exploring the national park and visiting the arts centre.
2 Bedroom Accommodation In Helmsley - Helmsley
No reviews

2 Bedroom Accommodation In Helmsley

cottage, Helmsley
Ryegate Cottage, a two-bedroom holiday home in central Helmsley, is located 150 meters from independent shops and pubs, and within walking distance of Helmsley Castle and the Walled Garden.
This pet-friendly accommodation for four guests features a well-equipped kitchen with a Rangemaster cooker, a sitting room with an open fireplace, a spacious back garden with a patio and lawn, and serves as an ideal base for exploring the North Yorkshire Moors National Park, with Duncombe Park nearby and the historic city of York a short drive away.

Frequently asked questions about cottages in Helmsley

  • What would be a good 1-day itinerary for visiting in and around Helmsley?

    You could start the day with a stroll around Helmsley's market square, stopping for a coffee and a pastry at the Helmsley Bakehouse. Then, head to the Helmsley Castle, a Norman ruin with a fascinating history. In the afternoon, explore the beautiful grounds of Duncombe Park, a stately home with a deer park and a cafe. For a final treat, visit the Helmsley Walled Garden, a tranquil oasis with a variety of plants and flowers.
  • What are the best cottages in Helmsley?

  • What are the can't-miss sights in Helmsley?

    You definitely need to see Helmsley Castle, a Norman ruin with a rich history. The market square is also a must-see, with its charming cobbled streets and historic buildings. For nature lovers, the Helmsley Walled Garden is a tranquil oasis with a variety of plants and flowers. If you're looking for something a bit more active, Duncombe Park offers beautiful walks and stunning views.
  • What are the best cottages with a pool in Helmsley?

    The best cottage with a pool in Helmsley is Cottage ∙ 7 Bedrooms ∙ 20 Guests.

  • Can you easily explore Helmsley on foot or by bike?

    Helmsley is a very walkable town. You can easily explore the market square, the castle, and the surrounding areas on foot. There are also plenty of bike paths in the area, so you can explore the countryside at your own pace. If you're looking for a longer ride, the Ryedale Cycleway is a great option, offering scenic views of the North York Moors.
  • What are the best cottages with a jacuzzi in Helmsley?

  • What activities are available in and around Helmsley?

    There's something for everyone in Helmsley! You can go for a walk in the beautiful countryside, visit the Helmsley Walled Garden, explore the market square, or take a tour of Helmsley Castle. For a more active day, you can go hiking in the North York Moors, go fishing in the River Rye, or play a round of golf at the Helmsley Golf Club. In the evening, you can enjoy a meal at one of the many restaurants in town or visit the local pub.
  • What are the best cottages for families and kids in Helmsley?

  • What famous towns or cities are near to Helmsley?

    Helmsley is ideally located near several other popular destinations. You can easily visit York, a historic city with a Roman past, and the vibrant city of Leeds, known for its shopping and nightlife. For a taste of the coast, Whitby is a charming seaside town famous for its fish and chips. You can also visit the beautiful Yorkshire Dales National Park, just a short drive away.
  • What are the best pet friendly cottages in Helmsley?

  • What are the most common amenities in cottages in Helmsley?

    Most cottages in Helmsley offer a range of amenities, including central heating, a fully equipped kitchen with an oven, hob, microwave, and fridge-freezer. Many cottages also have a washing machine, tumble dryer, and a TV. Some cottages may also offer a fireplace, a garden, or a patio.
  • What are the best cottages with parking in Helmsley?

Popular destinations

Best Helmsley cottages with a jacuzzi

Among the 56 accommodations in Helmsley, here are the 1 best cottages with a jacuzzi

3 Bed In Kirkbymoorside (Oc-g0001) - Helmsley
No reviews

3 Bed In Kirkbymoorside (Oc-g0001)

cottage, Kirkbymoorside
This detached cottage near Kirkbymoorside offers countryside views of the North York Moors, with walking paths and the town's gallery, antique shops, and market within 1.6 kilometers.
This opulent property accommodates six guests across three en-suite bedrooms, featuring a galley kitchen with a dishwasher, a private garden with a hot tub, and shared facilities including a tennis court and billiards room.

Best Helmsley cottages with a fireplace

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

2 Bed In Helmsley (Oc-g0037)

cottage, Helmsley
This two-bedroom holiday let in Helmsley is located within easy reach of the village's independent shops, cafes, and dining, and is situated just 800 metres from Helmsley Castle and a short walk from Helmsley Walled Garden, offering convenient access to the North York Moors National Park. This property accommodates up to three guests and features a wood burner, Wi-Fi, a well-equipped kitchen with a dishwasher, and two garden areas, including a patio with a BBQ, with off-road parking for one vehicle provided.
Cottage In Wass, Near Ampleforth - Helmsley
10 1 review

Cottage In Wass, Near Ampleforth

cottage
This country cottage is situated in Wass Village, within the North Yorkshire Moors National Park and Area of Outstanding Natural Beauty, a 5-minute walk from Wass Bank.
The accommodation sleeps six guests in three bedrooms, featuring two bathrooms, a gated garden with a BBQ, and is located opposite The Stapylton Arms Pub.
3 Bed In Helmsley (Oc-82891) - Helmsley
No reviews

3 Bed In Helmsley (Oc-82891)

cottage, Helmsley
This three-bedroom holiday home, accommodating up to four guests, is located in historic Helmsley, just 320 meters from the market square and within easy reach of the North York Moors National Park.
This secluded property offers a private south-facing courtyard, an open fire in the lounge/diner, and direct access to walking and cycling routes, with a well-equipped country-style kitchen featuring a microwave oven and dishwasher.
29 Bondgate - Helmsley
No reviews

29 Bondgate

cottage, York
This pet-friendly cottage near Helmsley, North Yorkshire, is less than 0.8km from the North York Moors National Park and Helmsley Arts Centre, and under 1.6km from Duncombe Park and the Cleveland Way.
The self-catering property offers free Wi-Fi, parking, a dishwasher, and a garden; nearby activities include exploring the national park and visiting the arts centre.
©2026 cozycozy.com