Photo by Mark Stacevich

Pickering holiday rentals

We found 707 holiday rentals — enter your dates for availability
Select from 27 homes, 165 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 Castle: Explore the impressive Pickering Castle, a key landmark offering insights into the town's rich heritage.
  • Picturesque Landscapes: Enjoy scenic views and natural beauty that perfectly complement Pickering’s historical charm.
  • Local Culture: Immerse yourself in the town’s vibrant local culture, ideal for both romantic getaways and family adventures.
  • Quaint Streets: Wander through charming streets that reflect Pickering’s blend of relaxation and rugged beauty.
  • Outdoor Adventures: Engage in a variety of outdoor activities, making the most of the town’s stunning natural settings.

Popular types of accommodation in Pickering

Welcome to Pickering, a charming market town nestled in North Yorkshire, England. Known for its picturesque landscapes and rich history, Pickering boasts attractions such as the iconic Pickering Castle and the delightful North Yorkshire Moors Railway. Whether you prefer a cosy cottage, a private holiday home, or a stylish apartment, you’ll find a variety of holiday rentals to suit your needs. Enjoy competitive nightly prices and immerse yourself in the local culture and experiences that Pickering has to offer.

  • Cottages: Enjoy the charm of cosy cottages, the top choice for a traditional Pickering retreat.
  • Private Holiday Homes: Experience the luxury of private holiday homes for an exclusive, homely stay.
  • Apartments: Modern apartments offer a contemporary base for your Pickering adventures.
  • Caravan Parks: Caravan parks provide a unique, outdoor holiday experience in scenic surroundings.
  • Condos: Stylish condos present a compact, chic option for your Pickering visit.**

Top attractions in and around Pickering

Pickering, England, is a charming town perfect for outdoor and adventure holidays, offering stunning scenery and rich history. Key attractions include the impressive Pickering Castle, a historic landmark that provides insights into the region's past. Visitors can also enjoy the picturesque landscapes and immerse themselves in the local culture, making it an ideal destination for couples seeking romance or families looking for memorable experiences. The town's blend of scenic beauty and historical significance ensures there's something for everyone.

  • North Yorkshire Moors Railway: This historic railway offers a charming journey through the stunning moorland scenery, allowing visitors to experience the rich culture and heritage of the area while enjoying steam train rides.
  • Flamingo Land Theme Park and Zoo: Just a short distance away, this theme park combines thrilling rides with a zoo, providing a fun-filled day for families, complete with educational exhibits and exciting attractions.
  • North York Moors National Park: A bit further out, this expansive park boasts breathtaking landscapes, outdoor adventures, and scenic walks, ideal for nature lovers and those seeking adventure.

Things to do recommended for couples

Discover a charming escape in Pickering. Enjoy a delightful countryside stroll, cosy dining experiences, and intimate picnics in picturesque parks. Embrace the local culture with guided heritage walks, perfect for a couple seeking a unique, romantic retreat.

Things to do recommended for families

Families visiting Pickering can enjoy a thrilling ride on the North Yorkshire Moors Railway and explore the fascinating exhibits at the Beck Isle Museum. Don’t miss the chance to wander through the picturesque Pickering Castle for a fun-filled day of history and adventure.

Things to do recommended for groups

Groups visiting Pickering can experience the thrill of motorsport at Oliver's Mount Racing, located 24km away. This exciting venue offers an adrenaline-filled atmosphere, perfect for those seeking adventure and camaraderie among friends in the picturesque Yorkshire countryside.

*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

Whether you're travelling with a group, as a family, with your pets, or seeking longer stays, be sure to set the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Pickering with a group: Consider the number of bedrooms required, along with facilities such as a fully-equipped kitchen or an outdoor area suitable for group gatherings. Luckily, you can filter for all of these features, and more, on Stayz.
  • Traveling to Pickering with young kids: Traveling with young children can be challenging. You need to prioritise their comfort and safety, as well as ensure the availability of age-appropriate amenities, such as a private swimming pool. It's also wise to consider the proximity to family-friendly attractions.
  • Taking your pets with you to Pickering: For many, a family holiday is not complete without their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most of these accommodations provide feeding bowls and beds, ensuring that every member of the family feels perfectly at home.
  • Planning for a long term stay visiting Pickering: If you are seeking holiday lets with discounts for extended stays of a month or more, you have come to the right place. With a simple filter, you can effortlessly locate and save on monthly rentals. Consider including a parking space, a well-equipped kitchen or a private pool in your search as well.

Where to stay in and around Pickering

Discover Pickering's rich historical charm and outdoor adventures. Explore its scenic landscapes, wander through quaint streets, and immerse yourself in its cultural heritage. Enjoy the friendly atmosphere and the unique blend of relaxation and rugged beauty that characterises this delightful town. Perfect for a holiday in Pickering, the city offers a mix of historical intrigue and natural splendour, making it an ideal destination for an unforgettable escape.

  • Thornton Dale: Nestled within the Pickering area, Thornton Dale is a charming village that invites visitors to immerse themselves in the great outdoors. Its diverse landscape provides a spectacular backdrop for adventure and scenic exploration. Enjoy a blend of recreational parks, amusement attractions, and expansive resort areas. Nearby, natural wonders such as national state parks, a national park, and a railway museum offer a rich tapestry of cultural and natural heritage, ensuring that every journey here is filled with memorable moments.
  • Kirby Misperton: Located a short distance from Pickering, Kirby Misperton offers an ideal setting for family adventures and outdoor pursuits. This quaint village is surrounded by an array of recreational spaces and amusement attractions that cater to all ages. Travellers can explore well-known theme parks, national parks, and national state parks in the vicinity, making it a delightful destination for those seeking a blend of lively activities and the tranquillity of nature.
  • Rosedale Abbey: Set within the Pickering area, Rosedale Abbey is a picturesque village celebrated for its scenic and adventurous atmosphere. This locale offers a unique combination of outdoor recreational spaces, artistic venues, and shopping centres that cater to diverse interests. The presence of national parks, national state parks, and historical monuments enriches the visitor experience, promising an engaging and culturally vibrant holiday for those looking to explore beyond the usual tourist trails.

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 Stayz is simple

Are you hoping to cut costs on your next holiday? Being flexible with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a convenient area to create new journeys, resume where you left off, or review and organise your plans. You will find properties you have saved or reserved categorised as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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)
  • Ganton Golf Club (12 mi / 19.3 km)
  • Ampleforth College Golf Club (12.2 mi / 19.7 km)
  • The Moors National Park Centre (16.1 mi / 25.9 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)
  • Hemsley Walled Garden (11.7 mi / 18.8 km)
  • Peasholm Park (15.2 mi / 24.4 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Pickering holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pickering holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Pickering holiday homes?
You can find great discounts on holiday homes in Pickering on Stayz, 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 change or cancel my Pickering holiday home booking on Stayz?
To find Pickering holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pickering?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Pickering holiday home?
Book your Pickering holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pickering?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pickering to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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