Photo by Mark Stacevich

Pickering holiday lettings

We found 705 holiday rentals — enter your dates for availability
Select from 31 homes, 167 cottages and other holiday rentals in Pickering to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, such as parking and air conditioning. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
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Why visit Pickering

  • Historic Pickering Castle: Explore the impressive remains of Pickering Castle, a key landmark showcasing the town's rich heritage.
  • Scenic North York Moors: Enjoy outdoor adventures in the stunning landscape of the North York Moors, perfect for leisurely walks.
  • Charming Market Town: Stroll through Pickering’s delightful streets filled with traditional shops and cosy cafés.
  • North Yorkshire Moors Railway: Experience a nostalgic train journey through picturesque countryside on this historic railway.
  • Breathtaking Vale of Pickering: Discover the scenic beauty of the Vale, ideal for peaceful strolls amid friendly locals.

Popular types of accommodation in Pickering

Welcome to Pickering, a charming market town nestled in the heart of North Yorkshire. Known for its rich history and stunning landscapes, Pickering offers a delightful array of attractions, including the iconic Pickering Castle and the picturesque North Yorkshire Moors Railway. Whether you're seeking a cosy cottage, a private holiday home, or a stylish apartment, you'll find an array of accommodation options perfect for your stay. Explore the beauty and charm of Pickering while enjoying the comforts of a home away from home.

  • Cottages: The top choice for visitors, these charming homes offer a cosy retreat in the heart of nature.
  • Houses: These spacious properties provide privacy and comfort, ideal for families or groups.
  • Apartments: Perfect for couples or solo travellers, these stylish lodgings offer convenience and urban living.
  • Caravan Parks: A popular option for those seeking a fun, outdoor experience with facilities for camping.
  • Condos: These modern accommodations blend comfort and luxury, perfect for a relaxing getaway.**

Top attractions in and around Pickering

Pickering, located in North Yorkshire, England, offers a delightful blend of outdoor adventure and rich history. Visitors can explore the impressive Pickering Castle, a historic landmark that provides insight into the region's past. The charming town also serves as a gateway to the stunning scenery of the North York Moors, ideal for leisurely walks and romantic outings. With its captivating attractions, Pickering is perfect for those seeking culture and adventure in a picturesque setting.

  • North Yorkshire Moors Railway: Experience a nostalgic journey on this historic steam railway, travelling through stunning moorland scenery. The vintage carriages and charming stations offer a glimpse into the past, making it a delightful outing for all ages.
  • Flamingo Land Theme Park and Zoo: Enjoy a fun-filled day at this family-friendly theme park featuring thrilling rides and a diverse zoo. It's perfect for both adrenaline seekers and those looking to explore wildlife in a vibrant setting.
  • North York Moors National Park: Discover the breathtaking landscapes of this national park, ideal for hiking, cycling, and enjoying the great outdoors. Its dramatic scenery and rich wildlife provide endless opportunities for adventure and relaxation.

Things to do recommended for couples

For a romantic getaway in Pickering, explore the charming streets hand-in-hand, visit the historic Pickering Castle, and enjoy a scenic ride on the North Yorkshire Moors Railway. Don't miss a delightful meal at a cosy local pub, perfect for creating cherished memories together.

Things to do recommended for families

Families will delight in exploring the enchanting Pickering Castle, where history comes alive, or enjoy a scenic steam train ride on the North Yorkshire Moors Railway. Additionally, the nearby Dalby Forest offers exciting trails and adventure activities perfect for all ages.

Things to do recommended for groups

Experience the thrill of Oliver's Mount Racing, a renowned motorsport venue located 24km from Pickering. Enjoy the adrenaline rush as you and your group immerse yourselves in the exciting atmosphere of this unique racing event.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you’re travelling with a group, as a family, bringing your pets, or seeking longer stays, be sure to apply the appropriate filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pickering with a group: Think about how many bedrooms you require, as well as any amenities you might want, like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Pickering with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pickering: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pickering: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Pickering

Pickering, nestled in North Yorkshire, offers a delightful blend of history and natural beauty. Explore the charming streets lined with traditional shops and cafés, and venture into the stunning North York Moors for outdoor adventures. Don't miss the enchanting Pickering Castle, which stands as a testament to the town's rich heritage. The Vale of Pickering provides breathtaking scenery, perfect for a relaxing escape or a scenic stroll among friendly locals.

  • Thornton Dale: Nestled close to Pickering, Thornton Dale is a charming village renowned for its stunning outdoor scenery and adventurous spirit. This picturesque locale offers visitors a wealth of recreational activities, from leisurely walks through its scenic trails to exciting adventures in nearby national parks. The village's proximity to the North York Moors National Park and the Ryedale Folk Museum makes it an ideal base for exploring the natural beauty and rich history of the region. With delightful local shops and cafés, Thornton Dale invites you to relax and soak in the serene ambiance.
  • Allerston: Just a stone's throw from Pickering, Allerston is a tranquil village that serves as a gateway to outdoor adventures and breathtaking scenery. The surrounding countryside boasts lush forests and rolling hills, perfect for hiking, cycling, and picnicking. Golf enthusiasts will appreciate the nearby golf courses that provide a perfect blend of sport and nature. The area's close proximity to the North York Moors National Park further enhances the allure of Allerston, making it a wonderful spot for those seeking connection with nature and the great outdoors.
  • Kirby Misperton: Located approximately 5km from Pickering, Kirby Misperton is a delightful village that offers a family-friendly atmosphere and a range of outdoor activities. The village is famous for its amusement park, which provides endless fun for visitors of all ages. Nearby attractions include the thrilling Flamingo Land Theme Park and the scenic landscapes of the North York Moors National Park. With its mix of recreational areas and relaxing resorts, Kirby Misperton is the perfect destination for families looking to create lasting memories while exploring the stunning Yorkshire countryside.

Best time to go to Pickering

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.3°F (3.5°C)Light RainMostly CloudySlightly LowSlightly 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 CloudyAverageAverage
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 HighAverage
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 simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, opting for a longer stay can often result in substantial 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: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up right where you left off, or review and arrange your travel plans. You'll find properties you've previously saved and booked conveniently sorted into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The cosy city of Pickering awaits you

Enjoy the culture and other features of Pickering. Renowned for its gardens, forests and camping, this city welcomes all visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Pickering

Do you want to discover attractions to see in the city? Venture out of your cosy holiday rental and experience everything that Pickering has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Flamingo Land Theme Park and Zoo (2.7 mi / 4.3 km)
  • Oliver's Mount Racing (14.9 mi / 24 km)
  • Alpamare (15.1 mi / 24.2 km)
  • Whitby Golf Club (18.1 mi / 29.1 km)
  • Ganton Golf Club (12 mi / 19.3 km)
  • Ampleforth College Golf Club (12.2 mi / 19.7 km)

Exploring the natural features in Pickering

Whether you're looking for adventure or just want to spend some time taking in the scenery, Pickering is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Dalby Forest Visitor Centre (4.3 mi / 7 km)
  • Mallyan Spout Waterfall (10.8 mi / 17.4 km)
  • Howardian Hills (11 mi / 17.7 km)
  • North York Moors National Park (11.7 mi / 18.8 km)
  • Peasholm Park (15.2 mi / 24.4 km)
  • North Bay Beach (15.3 mi / 24.7 km)

Transport to and around Pickering

The nearest airport is in Durham (MME-Teesside Intl.), located 32.2 mi (51.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Leeds (LBA-Leeds Bradford), which is 44.2 mi (71.1 km) away.

If you'd prefer to travel by train, you can make your way to Pickering Levisham Station.

Frequently asked questions

What is the best area to stay in Pickering when booking a holiday rental?
When considering a holiday rental in Pickering, a delightful market town in North Yorkshire, the area around the town centre is highly recommended. This central location provides easy access to a variety of amenities and attractions, making it convenient for visitors looking to explore.One of the key highlights nearby is the stunning Pickering Castle, a historic Norman fortification that offers fascinating insights into the region's past. Additionally, the North Yorkshire Moors Railway, which departs from the town, is a charming way to experience the scenic beauty of the surrounding moors and countryside.In terms of accommodation, the town centre boasts a range of properties, from cosy cottages to more modern apartments, suiting different preferences and group sizes. This variety ensures that visitors can find a suitable place to stay while enjoying the vibrant setting of Pickering, with its quaint shops, cafes, and restaurants all within walking distance.
How much does it cost to rent a holiday home in Pickering?
Prices for holiday rentals in Pickering 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 Pickering 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 Pickering holiday house rentals?
You can find great discounts on house rentals in Pickering 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.
What is the most popular type of holiday rental accomodation in Pickering?
In Pickering, cottages are the most popular type of holiday rental, with approximately 744 available throughout the charming town and its scenic surroundings. These cottages often provide a cosy atmosphere, featuring amenities such as fully equipped kitchens, comfortable living areas, and often beautiful gardens or outdoor spaces ideal for relaxation.For those seeking more space, there are around 128 holiday houses, which typically offer multiple bedrooms and larger living areas, making them great for families or groups wanting to explore the nearby North York Moors National Park. Additionally, about 108 chalets and 48 cabins can be found in the area, providing a rustic charm with amenities that include fireplaces and outdoor decking, ideal for enjoying the picturesque countryside.
Are there any family house rentals in Pickering?
In Pickering, there are numerous family-friendly house rentals available, with around 124 options to choose from. This charming town, located near the stunning North York Moors National Park, offers a variety of properties suitable for families. Many homes feature spacious living areas, full kitchens for preparing family meals, and gardens where children can play and explore.Visitors can enjoy the convenience of amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay. The town itself is rich in history, with attractions like the Pickering Castle and the North Yorkshire Moors Railway nearby, providing plenty of opportunities for family outings.
Can I rent a holiday home with a pool or hot tub in Pickering?
In Pickering, there are several holiday homes available for rent that include pools or hot tubs, making it a delightful destination for travellers seeking relaxation. This charming market town, located near the North York Moors National Park, offers a mix of properties, from modern villas to traditional cottages. Many rentals feature private pools, hot tubs, and outdoor seating areas, superb for unwinding after a day of exploring the beautiful countryside.In addition to the pool amenities, guests can expect fully equipped kitchens, cosy living spaces, and gardens that allow for outdoor dining. Find your rental in Pickering with a pool or a hot tub.
Can I find long-stay holiday rentals in Pickering?
A long-stay holiday rental in Pickering 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 pet-friendly house rentals in Pickering?
In Pickering, there are numerous pet-friendly house rentals available, with around 163 options to choose from. Many of these properties offer a variety of amenities that cater to the needs of both guests and their furry companions. Expect to find well-equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The area is known for its proximity to the stunning North York Moors National Park, which provides ample opportunities for outdoor adventures with your pets, including scenic walks and hiking trails. Additionally, many local attractions, such as the charming town centre with its quaint shops and cafes, are welcoming to pets, making Pickering an ideal destination for those travelling with animals. See all pet-friendly rentals in Pickering.
Are there any remote work holiday rentals in Pickering?
In Pickering, there are plenty of remote work holiday rentals available, with around 1,012 options to choose from. This charming market town in North Yorkshire provides a picturesque setting for those looking to combine work and leisure. Many rentals offer amenities tailored for remote workers, such as free Wi-Fi, designated laptop workspaces, and comfortable living areas conducive to productivity.Situated close to attractions like the historic Pickering Castle and the stunning North York Moors National Park, these properties allow guests to enjoy both a productive work environment and the beauty of nature. Many homes also feature fully equipped kitchens and outdoor spaces, superb for taking breaks or unwinding after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pickering holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pickering 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.
What are popular rental amenities in Pickering?
In Pickering, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties are also pet-friendly, welcoming travellers with furry companions. Onsite parking is commonly available, making it convenient for those driving to the area. Additionally, some rentals feature fireplaces, providing a cosy atmosphere during cooler evenings.
When is the best time to visit Pickering for a holiday rental?
The best time to book a holiday rental in Pickering is during the peak season from July to September. This period attracts numerous visitors who come to enjoy the charm of this historic market town and the surrounding North York Moors National Park. With pleasant temperatures averaging between 15 to 20 degrees Celsius, it's an ideal time for outdoor activities such as hiking, cycling, and exploring the picturesque scenery.July stands out as the most popular month, offering a vibrant setting filled with various local events and festivals. You'll find the town bustling with life, making it a great time to immerse yourself in the community spirit. Families and adventure seekers alike can take part in activities and enjoy the beautiful landscapes that Pickering has to offer.For those mindful of their budget, November presents a wonderful opportunity. While it's outside the peak tourist season, this month allows for a quieter experience. Visitors can appreciate the stunning autumn foliage and enjoy a more peaceful exploration of the local attractions without the crowds.
How early should I book a Pickering holiday rental?
Book your Pickering 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 Pickering?
In Pickering, visitors can take part in the charm of this historic market town. One of the top attractions is the stunning Pickering Castle, a Norman fortress offering rich history and beautiful views of the surrounding area. The town is also known for the North Yorkshire Moors Railway, where travellers can enjoy scenic steam train rides through the breathtaking North York Moors National Park.For those interested in local culture, the Beck Isle Museum showcases the history of Pickering and its surrounding areas, featuring fascinating exhibits and artefacts. Additionally, the nearby Dalby Forest provides ample opportunities for outdoor activities such as hiking, cycling, and wildlife spotting, making it a superb destination for nature enthusiasts.The vibrant market square, with its array of shops, cafes, and restaurants, is another highlight, offering a delightful atmosphere for visitors to explore and enjoy local delicacies.
Can I change or cancel my Pickering home rental booking on Vrbo?
To find Pickering 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 Pickering 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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