Helmsley holiday lettings

We found 536 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Helmsley that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, including parking and a TV. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Helmsley

  • Historic Helmsley Castle: Explore the ruins of this medieval castle, offering a glimpse into the town's rich heritage.
  • Charming market town atmosphere: Stroll through Helmsley’s quaint streets, filled with delightful shops and a friendly, welcoming vibe.
  • Stunning Yorkshire countryside: Enjoy scenic walks and outdoor activities amidst the picturesque landscapes surrounding Helmsley.
  • Diverse accommodation options: Choose from cosy cottages to modern self-catering stays, ensuring a comfortable visit.
  • Cultural experiences: Immerse yourself in local history and enjoy nearby historic houses and attractions.

Popular types of accommodation in Helmsley

Discover the charm of Helmsley with our diverse selection of holiday rentals. Whether you prefer cosy cottages, houses, or modern apartments, we have the perfect option for your getaway. Our popular Helmsley holiday cottages and self-catering accommodations cater to all types of travellers, ensuring you have a comfortable and memorable stay. Explore the picturesque surroundings while enjoying the savings and reassurance our platform offers.

  • Cottages: The top choice for holiday accommodation in Helmsley, offering charming and traditional stays.
  • Houses: A popular option for groups or families seeking a home-like atmosphere during their visit.
  • Apartments: Ideal for those wanting a self-contained space with convenient amenities in the heart of Helmsley.
  • Caravan Parks: Great for a unique outdoor experience, perfect for families and those who enjoy nature.
  • Cabins: A delightful choice for a rustic retreat, nestled in scenic surroundings.**

Top attractions in and around Helmsley

Helmsley, a charming market town, is perfect for outdoor and adventure holidays, offering stunning scenery and a rich cultural experience. Key attractions include the historic Helmsley Castle, a visitor centre, and nearby historic houses, making it an ideal destination for families and culture enthusiasts alike. Enjoy exploring the picturesque surroundings and immerse yourself in the local heritage during your visit to this delightful part of York, England.

  • Flamingo Land Theme Park and Zoo: A vibrant theme park and zoo located 6.2km from Helmsley, Flamingo Land offers thrilling rides, entertaining shows, and a chance to see exotic animals, making it perfect for families seeking fun and adventure.
  • Rievaulx Abbey: Situated 1.9km away, Rievaulx Abbey showcases stunning ruins steeped in history and culture. Visitors can explore the serene grounds and marvel at the impressive architecture, immersing themselves in the tranquil atmosphere.
  • Hemsley Walled Garden: Nestled within Helmsley, this delightful private garden provides a peaceful retreat. With friendly staff and secluded spots, it's an ideal location for relaxation and enjoying the beauty of nature.

Things to do recommended for couples

For a romantic getaway in Helmsley, indulge in a soothing treatment at Aldwark Manor Spa, located 9.9km away. With its serene atmosphere, it’s the perfect spot for couples to unwind and reconnect amidst beautiful surroundings.

Things to do recommended for families

Families will have an exciting time at Battlezone Paintball, just 10.6km from Helmsley, and can unwind at Rawcliffe Country Park, 11.2km away. For sports enthusiasts, Bootham Crescent Stadium, located 11.8km from Helmsley, offers a fantastic atmosphere for enjoying local matches.

Things to do recommended for groups

Embark on the Cleveland Way for a scenic hike, enjoy a round at Ampleforth College Golf Club, or catch a performance at York Theatre Royal for a taste of culture and entertainment. Helmsley offers a delightful mix of outdoor adventure and local charm for your group.

What do I need to keep in mind when booking a vacation in 'Helmsley

If you're travelling with a group, family, pets, or planning an extended stay, be sure to filter according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Helmsley with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Helmsley with young kids: Journeying with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, such as a private swimming pool. Additionally, it would be wise to factor in your closeness to attractions that cater to families.
  • Taking your pets with you to Helmsley: For many, a family holiday feels incomplete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Helmsley: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Helmsley

Helmsley, a charming market town nestled in the picturesque Yorkshire countryside, offers a delightful escape for those seeking relaxation and adventure. With its quaint cottages and historical ambiance, visitors can immerse themselves in the friendly, family-friendly atmosphere. Explore the stunning scenery, enjoy leisurely walks, and savour the local delights, all while experiencing the perfect blend of seclusion and luxury. Helmsley promises a memorable getaway, whether you're wandering the market or venturing into the surrounding landscapes.

  • Harome: Harome is a picturesque village situated approximately 1.2km from Helmsley, known for its stunning rural landscapes and outdoor adventures. This charming locale offers visitors a chance to immerse themselves in nature with its nearby national park and historic sites. Outdoor enthusiasts will find ample opportunities for recreation, including scenic walks and cycling routes. Harome also boasts a renowned spa for those seeking relaxation and rejuvenation, making it a perfect destination for both adventure seekers and those looking to unwind.
  • Nawton: Located just 1.2km from Helmsley, Nawton is another delightful village that invites visitors to explore its beautiful surroundings. This area is popular for outdoor pursuits and offers a wealth of scenic views. Visitors can enjoy a variety of activities, including visits to local amusement parks and resorts, which cater to families and thrill-seekers alike. The nearby national park and historic landmarks add to Nawton's appeal, providing a rich blend of nature and culture for tourists to discover.
  • Rievaulx: Rievaulx is a charming village located about 1.9km from Helmsley, renowned for its picturesque scenery and outdoor experiences. The village is an ideal spot for those looking to explore the great outdoors, with excellent recreational areas and opportunities for swimming and spa treatments. Visitors can also immerse themselves in the rich history of the region, with national parks and historic sites conveniently located nearby, making Rievaulx a perfect blend of adventure and relaxation for any traveller.

Best time to go to Helmsley

If you're planning a trip to Helmsley, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.3°F (3.5°C)Light RainMostly CloudyAverageSlightly Low
February39.6°F (4.2°C)Light RainMostly CloudyAverageSlightly Low
March42.1°F (5.6°C)Light RainMostly CloudyAverageSlightly Low
April45.7°F (7.6°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May50.7°F (10.4°C)Light RainMostly CloudyAverageAverage
June56.1°F (13.4°C)Light RainMostly CloudyAverageAverage
July59.9°F (15.5°C)Light RainMostly CloudySlightly HighSlightly High
August59.5°F (15.3°C)Light RainMostly CloudyAverageSlightly High
September55.9°F (13.3°C)Light RainMostly CloudySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly CloudySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly CloudySlightly LowAverage
December40.1°F (4.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for planning your journeys, allowing you to seamlessly pick up from where you last paused or to review and arrange your travel plans. You can easily find the properties you’ve saved or booked, organised under sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to relaxing Helmsley

Enjoy the history and other features of Helmsley. Well known for its spas, parks and restaurants, this relaxing city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Helmsley

Do you want to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Helmsley a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Flamingo Land Theme Park and Zoo (10.4 mi / 16.8 km)
  • Aldwark Manor Spa (16.4 mi / 26.4 km)
  • Ampleforth College Golf Club (4.3 mi / 6.9 km)
  • Malton and Norton Golf Club (13.4 mi / 21.6 km)
  • Thirsk Birds of Prey Centre (15 mi / 24.1 km)
  • Aldwark Manor Golf Club (15.7 mi / 25.3 km)

Exploring the natural features in Helmsley

Whether you're looking for fun outdoor activities or just want to take in the scenery, Helmsley is a great spot to appreciate mother nature. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Hemsley Walled Garden (0.5 mi / 0.7 km)
  • National Trust Nunnington Hall (4.3 mi / 6.9 km)
  • Sutton Bank National Park Centre (6.1 mi / 9.9 km)
  • Howardian Hills (7.2 mi / 11.6 km)
  • Yorkshire Lavender (8.7 mi / 14 km)
  • Redwood Park Fishing Lakes (12.8 mi / 20.6 km)

Travelling to and around Helmsley

Fly into Durham (MME-Teesside Intl.), the closest airport, located 23.8 mi (38.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Leeds (LBA-Leeds Bradford), which is 35.8 mi (57.5 km) away.

Frequently asked questions

What is the best area to stay in Helmsley when booking a holiday rental?
When considering a holiday rental in Helmsley, the town centre is the best area to stay. This charming market town, located in the North York Moors, offers a delightful blend of history and natural beauty. Staying in the heart of Helmsley means you'll be within easy walking distance of its top attractions, such as the impressive Helmsley Castle, which dates back to the 12th century and provides a fascinating glimpse into the area's rich heritage. Additionally, the nearby Helmsley Walled Garden is a serene spot to explore, showcasing beautifully landscaped gardens and an array of plants.

In the town centre, you will find a variety of properties available, from quaint cottages to more modern apartments, suiting different preferences and group sizes. This central location not only provides convenient access to local shops, cafes, and restaurants, but it also serves as a great base for exploring the stunning landscapes of the North York Moors National Park.
How much does it cost to rent a holiday home in Helmsley?
Prices for holiday rentals in Helmsley vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Helmsley to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Helmsley holiday house rentals?
You can find great discounts on house rentals in Helmsley on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Helmsley?
A long-stay holiday rental in Helmsley is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Helmsley holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Helmsley with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Helmsley for a holiday rental?
The most popular time to visit Helmsley for a holiday rental is during the peak season from July to September. This vibrant period attracts visitors eager to explore the stunning North York Moors National Park, renowned for its picturesque landscapes and charming villages. Summer in Helmsley offers delightful weather, with temperatures typically ranging from 15 to 25 degrees Celsius, making it an ideal time for outdoor activities such as hiking, cycling, and leisurely strolls through the beautiful gardens.

July, in particular, is a bustling month, filled with events and activities that bring the community to life. Visitors will enjoy the warm atmosphere while exploring local attractions, including the historic Helmsley Castle and the quaint market square. This is also a fantastic time for food enthusiasts to indulge in local delicacies at the various cafes and restaurants.

For those seeking a more budget-friendly option, consider visiting in December. While the colder weather (averaging around 0 to 5 degrees Celsius) may deter some, this month offers a unique charm with festive decorations and a quieter ambiance. It's the superb time to enjoy peaceful walks through the wintry landscape and perhaps visit the Christmas markets for some local crafts and treats.

Ultimately, whether you prefer the lively summer months filled with activity or the serene winter atmosphere, Helmsley has something special to offer all year round.
How early should I book a Helmsley holiday rental?
Book your Helmsley holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Helmsley?
In Helmsley, visitors can enjoy a charming mix of historical and natural attractions. The iconic Helmsley Castle, dating back to the 12th century, offers a glimpse into the area's rich heritage and provides beautiful views of the surrounding countryside. Nearby, the picturesque Helmsley Walled Garden is a delightful spot for a leisurely stroll, showcasing a variety of plants and flowers in a serene setting.

For those interested in local culture, the Ryedale Folk Museum presents fascinating exhibits on the region's history and traditional crafts. Additionally, the North York Moors National Park is easily accessible from the town, offering stunning landscapes, walking trails, and opportunities for outdoor activities.
Can I change or cancel my Helmsley home rental booking on Vrbo?
To find Helmsley holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Helmsley holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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