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Helmsley vacation rentals
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Best Vacation rentals and Airbnb offers in Helmsley

Popular Family Vacation Rentals in Helmsley

Kid-friendly vacation rentals in Helmsley offer fresh air and hiking trails right outside your door for the perfect family retreat.

Ivy Cottage - Helmsley
9.5 10 reviews
Helmsley
07/13 – 07/17
$318/nighttotal: $1272 (4 )

Ivy Cottage

3 2
house , Helmsley
Ivy Cottage is located in Helmsley, a charming market town in the North Yorkshire Moors National Park, just a short walk from Helmsley Castle and 11 minutes from historic ruins. Guests consistently rate the cottage excellent for location, cleanliness, and overall experience.
This 3-bedroom home provides 1400 square feet of space for up to 5 guests. The cottage offers a fully equipped kitchen, a garden, free Wi-Fi, and parking.
Cliff Stud Retreat, Helmsley - Cecil Cottage - Helmsley
9.7 147 reviews
Helmsley
07/08 – 07/10
$236/nighttotal: $472 (2 )

Cliff Stud Retreat, Helmsley - Cecil Cottage

1 2
apartment , Helmsley
Cecil Cottage is located on a 220-acre estate just outside the charming town of Helmsley, providing easy access to its shops, pubs, and restaurants. This cottage is rated excellent for location, cleanliness, and overall user experience.
Cecil Cottage is a 3-bedroom, 1-bathroom home that comfortably sleeps up to 5 guests. Enjoy the private garden with fruit trees, the wood-burning stove for cozy evenings, and access to the estate’s grounds for leisurely walks.
St. Anthonys - Helmsley
Helmsley
08/04 – 08/07
$382/nighttotal: $1146 (3 )

St. Anthonys

3 4
apartment , Helmsley
This 3-bedroom, 1-bathroom apartment in Ampleforth village is a short drive from Helmsley, offering proximity to Ampleforth Abbey, Helmsley Castle, and the North York Moors National Park.
This family-friendly flat accommodates up to 5 guests with a full kitchen, a living room with a woodburner and Smart TV, free Wi-Fi, and a back garden with countryside views, ideal for exploring the Yorkshire area.
3 Bedroom Accommodation In Ampleforth, Near Helmsley - Helmsley
Helmsley
08/04 – 08/07
$382/nighttotal: $1146 (3 )

3 Bedroom Accommodation In Ampleforth, Near Helmsley

3 4
cottage , Ampleforth, near Helmsley
This Ampleforth cottage is located in a peaceful village, a short drive from Helmsley, offering proximity to Ampleforth Abbey, Helmsley Castle, and the North York Moors National Park.
This family-friendly rental accommodates up to 5 guests in 3 bedrooms and features a private garden with countryside views, a woodburner, smart TV, and a fully equipped kitchen-diner, with a travel cot and highchair provided.

Best Helmsley vacation rentals with a balcony

Harome Holidays - Helmsley
8.5 4 reviews
Helmsley
07/13 – 07/17
$208/nighttotal: $832 (4 )

Harome Holidays

2 2
house , Harome
Griff Lodge, a two-bedroom house in Harome, England, is 13 miles from Flamingo Land Theme Park, 20 miles from Dalby Forest, and 23 miles from York.
This 1,080-square-foot home features a fully equipped kitchen, a terrace, a garden, free parking, Wi-Fi, and accommodates up to seven guests, offering a peaceful garden setting with soundproofed rooms and a fireplace.
Rye Cottage - Helmsley
8.6 9 reviews
Helmsley
08/04 – 08/07
$615/nighttotal: $1845 (3 )

Rye Cottage

3 4
house , Helmsley
Rye Cottage is located in Helmsley, a market town in the North York Moors National Park, about 9 miles from Flamingo Land Theme Park and 12 miles from Dalby Forest.
This 3-bedroom, 3-bathroom vacation home features a fully equipped kitchen with a dishwasher, a washing machine, free Wi-Fi, private parking, a fireplace, and a garden, making it ideal for families or groups of friends.
Studford Luxury Lodges - Helmsley
Helmsley
08/04 – 08/07
$524/nighttotal: $1572 (3 )

Studford Luxury Lodges

3 4
chalet , York
This luxury lodge in North Yorkshire offers convenient access to the North York Moors National Park and Howardian Hills, with the Helmsley Arts Centre and National Trust Nunnington Hall within 5 miles.
This secluded chalet features 3 ensuite super king bedrooms accommodating up to 6 guests, a private hot tub, sauna, and a spacious deck with forest views, all equipped with full entertainment systems and home-like amenities.
Rye Court Cottage - Stunning Cottage In Central Helmsley With Parking - Helmsley
9.0 171 reviews
Helmsley
07/08 – 07/10
$479/nighttotal: $958 (2 )

Rye Court Cottage - Stunning Cottage In Central Helmsley With Parking

3 2
house , Helmsley
Rye Court Cottage is located in the center of Helmsley, just 15 miles from Flamingo Land Theme Park and 19 miles from Dalby Forest, making it an ideal base for exploring the Yorkshire countryside. This home has received excellent ratings for location, cleanliness, and overall experience.
The cottage has 3 bedrooms and 2 bathrooms, providing ample space for families or groups. It offers a fully equipped kitchen with a dishwasher, washing machine, and a cozy fireplace, as well as a terrace, garden, and parking.

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, with its impressive ruins and rich history. You can also visit the Helmsley Walled Garden, a beautiful example of a Victorian walled garden. A short drive away, you'll find the stunning Rievaulx Abbey, a former Cistercian monastery.
  • What are the best Airbnb and vacation rentals in Helmsley?

    Ryedale 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 through Helmsley, offering stunning views of the North York Moors. For a shorter walk, try the Helmsley to Rievaulx Abbey trail, which takes you through picturesque countryside. If you're a cyclist, the Ryedale Cycleway is a great option, offering a scenic route through the countryside.
  • What are the most popular Airbnbs in Helmsley?

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

    York, a historic city with a Roman past, is about a 40-minute drive from Helmsley. You can also easily reach the coastal town of Whitby, known for its dramatic cliffs and the famous Whitby Abbey, in about an hour's drive.
  • 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 amenities are commonly available in vacation rentals in Helmsley?

    Vacation rentals in Helmsley typically offer amenities like kitchens, living rooms, and bedrooms. Many also include features like Wi-Fi, washing machines, and dryers. Some rentals even have private gardens or patios.
  • What are the best rentals for families and kids in Helmsley?

  • What time of year is best to rent a vacation rental Helmsley?

    The best time to visit Helmsley depends on your preferences. The spring and fall offer mild weather and beautiful scenery, while the summer is ideal for outdoor activities. If you enjoy winter sports, then the winter months are a good choice.
  • 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, Crossing Cottage and The Old Bank.

  • What are the local dishes in Helmsley region?

    The area around Helmsley is known for its traditional Yorkshire dishes. Try a hearty Yorkshire pudding with roast beef and gravy, or a classic Yorkshire pie. You can also find delicious local cheeses and craft beers.

Destinations nearby

Best Helmsley vacation rentals with a sauna

Cottage ∙ 1 Bedroom ∙ 2 Guests - Helmsley
8.3 6 reviews
Helmsley
07/08 – 07/10
$372/nighttotal: $744 (2 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
cottage , Harome
Foxglove Cottage, a pet-friendly one-bedroom house, is located in the Ryedale district of North Yorkshire, England, near the North York Moors National Park and easily accessible to Helmsley and York.
This romantic, single-story dwelling offers a private patio, ocean-blue décor, a full kitchen with dishwasher, and a walk-in shower, accommodating up to two guests and boasting proximity to award-winning Harome inns, including a Michelin-starred restaurant.

Best Helmsley vacation rentals with a fireplace

Keldholme Cottage 1 - Uk10992 - Helmsley
10 17 reviews
Helmsley
06/27 – 06/28
$561/nightfor 1 night

Keldholme Cottage 1 - Uk10992

2 2
apartment , Kirkbymoorside
This Keldholme cottage, less than a mile from Kirkbymoorside and near the North York Moors National Park, offers easy access to Helmsley, Pickering, and York (under 40 minutes to York).
The two-bedroom, one-bathroom house sleeps three guests and includes a dishwasher, Wi-Fi, a wood-burning stove, a shared garden with a patio, and parking; two dogs are welcome.
Cosy Modern Home In Ampleforth Village - Helmsley
10 189 reviews
Helmsley
08/04 – 08/07
$196/nighttotal: $588 (3 )

Cosy Modern Home In Ampleforth Village

1 4
bungalow , Yorkshire du Nord
This recently renovated two-bedroom house is located in Ampleforth, North Yorkshire, a five-minute walk from local amenities and under a mile from St. Alban's Sports Centre, with Helmsley four miles away.
The 2-bathroom home features a fully equipped kitchen with Smeg appliances, a private patio with a BBQ, and accommodates up to four guests in its open-plan living space.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Helmsley
10 5 reviews
Helmsley
07/13 – 07/17
$184/nighttotal: $736 (4 )

Cottage ∙ 3 Bedrooms ∙ 5 Guests

3 2
cottage , Wass
The Burrows, a cottage, is located in Wass, North Yorkshire, approximately 7.5 miles from the market town of Helmsley and situated on the southern edge of the North York Moors National Park.
This three-bedroom rental accommodates up to five guests and features a woodburning stove, a garden, a kitchen with a fridge, microwave, and dishwasher, and a master bedroom with an en-suite and a balcony offering countryside views.
29 Bondgate - Helmsley
9.1 14 reviews
Helmsley
08/04 – 08/07
$305/nighttotal: $915 (3 )

29 Bondgate

3 4
apartment , Helmsley
This charming 2-bedroom cottage is located just a short walk from Helmsley's market square and the historic Helmsley Castle. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The cottage comfortably sleeps four guests and features a well-equipped kitchen with modern appliances, a cozy living area with a wood-burning stove, and a luxurious clawfoot bath. Guests can enjoy a multi-level rear garden with a patio, lawn, furniture, and a barbecue, making it perfect for relaxing and enjoying the Yorkshire weather.
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