Compare Vacation Rentals & Airbnb in Helmsley

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Helmsley vacation rentals
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119 Rentals and Airbnb in Helmsley

Best family friendly Helmsley vacation rentals

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

Cottage ∙ 4 Bedrooms ∙ 8 Guests - Helmsley
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Helmsley
Holly-Garth, a four-bedroom house in Helmsley, North Yorkshire, is situated close to Helmsley Castle and the Helmsley Walled Garden, offering easy access to these attractions.
This self-catering property sleeps eight guests and boasts two living rooms (each with a wood burner and Sky TV), a well-equipped kitchen/diner with a dishwasher, three bathrooms, a private enclosed patio with barbecue, private parking for three cars, a bike store, and a pool table in an outbuilding.
Saxon House - Helmsley
9.7 7 reviews

Saxon House

apartment
Saxon House, a dog-friendly detached stone property in Harome, North Yorkshire, is situated near the acclaimed restaurants The Pheasant and The Star Inn at Harome, and within easy reach of the North York Moors National Park.
This five-bedroom house, with a self-contained annexe, sleeps nine guests and offers a 1 square metre floor area, a well-equipped kitchen with dishwasher, ample parking, a south-facing garden, and a wood-burning stove; a high chair and travel cot are provided.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Helmsley
No reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, East End
St. Anthonys, a detached holiday home, is located in the village of Ampleforth, North Yorkshire, offering convenient access to Helmsley, 5 kilometers away, and the North York Moors National Park.
This family-friendly cottage sleeps five across three bedrooms and features a well-equipped kitchen, a living room with a woodburner, free Wi-Fi, and a garden with countryside views, with a travel cot and highchair provided.
Lily Pad - Uk49104 - Helmsley
10 11 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.

Best Helmsley vacation rentals with a balcony

The Old School House - Helmsley
10 1 review

The Old School House

house, Lastingham
The Old School House, a family-friendly holiday home in Lastingham, is situated 17.7 kilometres from Flamingo Land Theme Park and 20.9 kilometres from Dalby Forest.
This spacious 400 square meter property accommodates up to 15 guests, offering a fully equipped kitchen with a dishwasher and oven, free WiFi, and garden access, with cycling and hiking opportunities nearby.
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.
The Coppice Cabin - Helmsley
No reviews

The Coppice Cabin

cabin, Helmsley
The Coppice Cabin is situated in Helmsley, with Teesside International Airport located approximately 55 kilometres away.
This one-bedroom, two-guest lodge offers 30 square metres of living space, featuring a fully equipped kitchen, a hot tub, and barbecue facilities, ideal for a peaceful retreat.
Willows At Abbey Farm Cottage - Helmsley
No reviews

Willows At Abbey Farm Cottage

cabin, Rosedale Abbey
This Wind in the Willows themed shepherd's hut is situated in Pickering, just a short drive from Rosedale Abbey and the Ryedale Folk Museum, and within reach of Flamingo Land Theme Park and The Moors National Park.
This glamping accommodation for four features a private patio garden with a BBQ, fire pit, and wood-fired hot tub, a fully equipped kitchen, a log burner, and a private shower room, with ample space for pitching tents.

Frequently Asked Questions about vacation rentals in Helmsley

  • What are some interesting places to visit in or near Helmsley?

    Helmsley Castle is a must-see, a 12th-century fortress with stunning views. The Ryedale Folk Museum is great for learning about the local history and culture. If you're into gardens, the beautiful Helmsley Walled Garden is a treat.
  • What are the best Airbnb and vacation rentals in Helmsley?

    Bilsdale Cottage, Spacious House 3 Ensuite Bedrooms - Sleeps 6 - Centre Of Helmsley - Pet Friendly - and The Flat @ 2 Castlegate are the most popular Airbnb and vacation rentals in Helmsley among travelers.

  • Which walking or cycling routes are the best in Helmsley?

    The Cleveland Way National Trail passes right through Helmsley, offering scenic views. The Helmsley to Rievaulx Abbey walk is a classic, taking you through the beautiful Rievaulx Forest. For cycling, the Helmsley to Pickering route is flat and easy, perfect for a leisurely ride.
  • What are the most popular Airbnbs in Helmsley?

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

    Helmsley is a great base for exploring the North York Moors National Park. You can go hiking, cycling, horse riding, and even try your hand at rock climbing at the nearby Sutton Bank.
  • What are the best vacation rentals with a pool in Helmsley?

    The best vacation rental with a pool in Helmsley is The Helmsley Retreat.

  • What other towns or cities can be easily accessed from Helmsley?

    York is about a 45-minute drive away, and you can easily reach the historic city of Pickering in around 15 minutes. The market town of Thirsk is also within easy reach, about a 20-minute drive.
  • 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 a kitchen, a living room, and a bathroom. Many also offer amenities like Wi-Fi, a washing machine, and a dryer. Some even have a garden or patio.
  • What are the best rentals or Airbnbs with a jacuzzi in Helmsley?

    The best vacation rentals or Airbnb with a jacuzzi in Helmsley are The Pheasant, The Old Bank and The Helmsley Retreat.

  • 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 pleasant and the countryside is in bloom. Autumn is also a beautiful time to visit, with the changing colours of the leaves.

Popular destinations

Best Helmsley vacation rentals with a sauna

4 Bed In Slingsby (Oc-g0146) - Helmsley
No reviews

4 Bed In Slingsby (Oc-g0146)

apartment
This four-bedroom barn conversion is situated in Fryton, North Yorkshire, offering proximity to the Howardian Hills, 7 kilometres from Malton, 4 kilometres from Castle Howard, and 18 kilometres from York.
This family-friendly, pet-welcoming holiday cottage accommodates up to eight guests and features a private hot tub, a well-equipped kitchen with a dishwasher, and access to shared leisure facilities including a gym, sauna, and games room.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Helmsley
10 3 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Fryton
This Fryton, North Yorkshire holiday home is situated 11km from Malton and 6.4km from Castle Howard, offering easy access to these North Yorkshire attractions.
Sleeping eight in four super-king bedrooms (convertible to twins), this 45 square metre property boasts four bathrooms, a private hot tub, and shared access to a gym, sauna, and games room, alongside a well-equipped kitchen/diner and separate dining room.
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.
4 Bed In Slingsby Oc-g0146 - Helmsley
No reviews

4 Bed In Slingsby Oc-g0146

house, Hovingham
This four-bedroom house in Hovingham, North Yorkshire, is ideally located 16km from Flamingo Land Theme Park, 31km from York, and 34km from Dalby Forest.
The 45 square metre property boasts four bathrooms, a jacuzzi, spa, fitness centre, private garden, and parking, comfortably accommodating up to twelve guests with a fully equipped kitchen and free internet access.

Best Helmsley vacation rentals with a fireplace

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Helmsley
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Helmsley
This Helmsley cottage is situated in North Yorkshire, a short walk from Helmsley's market square and within easy reach of the North York Moors National Park.
The two-bedroom, two-bathroom property offers an open-plan living space with a wood-burning stove, private garden with sun room, and modern amenities including a dishwasher, Smart TVs, and free Wi-Fi; it sleeps four and provides on-road parking.
29 Bondgate - Helmsley
9.0 31 reviews

29 Bondgate

house, York
This charming house is located just 24km from York Train Station and 29km from Lightwater Valley Theme Park, offering a peaceful retreat while remaining close to the city's attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The house is ideal for families, with a spacious 105 square meter layout and a garden. Guests can enjoy modern conveniences like Wi-Fi, a fully equipped kitchen, and a comfortable living area, making it perfect for both relaxing and exploring the surrounding area.
2 Bed In Nr Helmsley (Oc-g0131) - Helmsley
8.0 1 review

2 Bed In Nr Helmsley (Oc-g0131)

apartment
This Grade II-listed converted church cottage, situated 2.4km from Helmsley town centre and 40km from York, offers spectacular views of the Yorkshire countryside and is close to the Howardian Hills and Castle Howard.
The property sleeps four, boasting two bedrooms (one king-size, one with a double sofa bed), two bathrooms (one family bathroom, one wet room), a spacious lounge/diner with a wood burner, a contemporary kitchen with dishwasher, and a garden with BBQ; pets are welcome.
Foxglove Cottage - Helmsley
8.2 9 reviews

Foxglove Cottage

house, York
Foxglove Cottage, a pet-friendly house near York, is situated approximately 22.5km from Flamingo Land Theme Park and 29km from Dalby Forest, with York Minster and York Train Station both 37km away.
This one-bedroom property, boasting 90 square metres of floor space, offers a fully equipped kitchen with dishwasher, private garden, free Wi-Fi, and private parking, perfect for exploring the Yorkshire countryside's cycling opportunities.
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