Pickering holiday lettings

We found 2,327 holiday rentals — enter your dates for availability

Select from 42 homes, 219 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.

Holiday rentals with weekly discounts - Pickering

Showing deals for:14 Nov - 21 Nov
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Find out more about Pickering

Find out more about Pickering

Why visit Pickering

  • Historic Attractions: Explore the medieval Pickering Castle and delve into the town's rich history.
  • Scenic Countryside: Enjoy breathtaking views of the Yorkshire countryside, perfect for outdoor adventures.
  • Charming Accommodations: Stay in delightful cottages or cosy holiday homes for a true Yorkshire experience.
  • Warm Hospitality: Experience the friendly atmosphere and welcoming nature of the local residents.
  • Picturesque Villages: Venture to nearby quaint villages that showcase the charm of rural England.

Popular types of accommodation in Pickering

If you're looking for the perfect getaway in Pickering, you're in luck! The most sought-after types of accommodation include charming cottages, private holiday homes, and comfortable apartments. Whether you're after traditional Yorkshire cottages or a cosy bedroom cottage, our selection of Pickering cottages promises a delightful stay tailored to your needs. Experience the beauty of this historic town while enjoying all the comforts of home.

  • Cottages: The most sought-after option for holiday stays in Pickering, offering a charming and cosy retreat.
  • Houses: A popular choice for those seeking spacious and comfortable accommodation, perfect for families or groups.
  • Apartments: Ideal for couples or solo travellers, these provide a convenient and self-contained environment.
  • Caravan Parks: A delightful way to experience the great outdoors, with various facilities and amenities.
  • Condos: A modern accommodation choice, combining comfort and convenience for your stay in Pickering.**

Top attractions in and around Pickering

Pickering is an ideal destination for those seeking outdoor adventures and beautiful scenery. Visitors can explore local attractions such as Pickering Castle and enjoy a mix of culture, history, and family-friendly experiences. With its charming surroundings, Pickering offers a delightful blend of historic buildings and natural beauty, ensuring a memorable holiday for all travellers.

  • Flamingo Land Theme Park and Zoo: Located 1.9km from Pickering, this vibrant theme park offers thrilling rides, entertaining shows, and a zoo featuring exotic animals, making it perfect for family fun and excitement.
  • North Yorkshire Moors Railway: Nestled within Pickering, this historic railway transports you back in time with its scenic steam train journeys through the stunning North York Moors, immersing you in rich local culture.
  • Dalby Forest Visitor Centre: Situated in Pickering, this visitor centre provides a gateway to outdoor adventure, with trails for walking and cycling, ideal for families seeking nature and exploration.

Things to do recommended for couples

For a romantic getaway in Pickering, explore the enchanting North York Moors National Park with a scenic walk, followed by a cozy evening at a charming local pub. Don't miss the steam train ride on the Pickering to Whitby line, offering stunning views and a touch of nostalgia.

Things to do recommended for families

Families can enjoy a thrilling day at Scarborough Cricket Club, located 9.3km from Pickering. The vibrant atmosphere and exciting sports vibes make it a perfect outing for all ages, offering a wonderful opportunity to experience local sporting culture.

Things to do recommended for groups

Groups visiting Pickering can enjoy a delightful evening at Scarborough Open Air Theatre, only 9.3km away, experience a round of golf at Malton and Norton Golf Club, 5.0km distant, or embark on an adventure along the scenic Cleveland Way hiking trail, situated 7.5km from the town.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Pickering with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for socialising. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Pickering with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, as well as access to suitable amenities, such as 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 families, a holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at the Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home during your stay.
  • Planning for a long term stay visiting Pickering: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly accommodation options. Don’t forget to include additional preferences in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in and around Pickering

Pickering, a charming market town, serves as a perfect base for exploring the stunning Yorkshire countryside. Visitors can immerse themselves in rich culture and history while enjoying the warm hospitality of friendly locals. From relaxing retreats to adventurous outings, Pickering offers a delightful mix of experiences, making it an ideal getaway for those seeking both seclusion and luxury. Venture nearby to discover picturesque landscapes and quaint villages that embody the spirit of rural England.

  • Thornton Dale: Nestled in the picturesque surroundings of Pickering, Thornton Dale is a charming village that offers an abundance of outdoor adventures and stunning scenery. As you wander through its scenic streets, you'll discover delightful local shops and cosy tearooms that invite you to relax and soak in the atmosphere. The village serves as an excellent base for exploring nearby attractions, including the breathtaking national park and expansive forests that are perfect for hiking and cycling. Families can enjoy recreational areas and an amusement park, making Thornton Dale an ideal destination for all ages seeking adventure amidst beautiful landscapes.
  • Rosedale Abbey: Just a stone's throw from Pickering, Rosedale Abbey is a serene village that combines outdoor exploration with historical charm. The village is surrounded by rolling hills and lush valleys, making it perfect for walking, cycling, and enjoying nature. Visitors can engage in various activities, including golf at a nearby recreation park and exploring the local national park. Rosedale Abbey is also home to notable monuments that reflect its rich history, providing a fascinating glimpse into the past while you enjoy the stunning scenery of the Yorkshire countryside.
  • Kirby Misperton: Located a short distance from Pickering, Kirby Misperton is a delightful village ideal for family outings and outdoor adventures. Known for its vibrant atmosphere, visitors can enjoy thrilling experiences at the nearby theme park, which offers a range of attractions for both children and adults. Additionally, Kirby Misperton boasts recreational areas perfect for picnics and leisurely walks. With its close proximity to national parks and beautiful landscapes, this village serves as an excellent destination for those looking to create lasting memories with family and friends amidst nature's beauty.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you aiming to save on your next getaway? It’s worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan exciting new getaways, pick up right where you left off, or manage your travel arrangements effectively. You can easily access properties you've saved or booked previously, now conveniently organised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply 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)
  • Malton and Norton Golf Club (8.4 mi / 13.5 km)
  • Ganton Golf Club (12 mi / 19.3 km)
  • Spa Cliff Lift (15.5 mi / 24.9 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)
  • North Riding Forest Park (5.8 mi / 9.3 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)

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, England, the best area to stay is the town centre. This charming area offers a delightful mix of history and convenience, making it an ideal base for exploring the surrounding attractions. You'll find a good selection of properties, with around 50 holiday rentals available, ranging from quaint cottages to modern apartments, suiting various preferences and budgets.
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 around 201 available in the area. These charming properties are often situated in scenic locations, providing a quintessential English countryside experience. Most cottages come with well-equipped kitchens, cosy living areas, and outdoor spaces, ideal for enjoying the peaceful surroundings.
Are there any family house rentals in Pickering?
In Pickering, there are plenty of family-friendly house rentals—approximately 121 available to choose from. This charming market town serves as a fantastic base for exploring the surrounding North York Moors National Park. Many properties in the area feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where children can safely play.

Visitors can enjoy amenities such as Wi-Fi, laundry facilities, and multiple bedrooms to accommodate larger groups. The town is known for its historic charm, with attractions like the picturesque Pickering Castle and the North Yorkshire Moors Railway nearby, making it easy for families to immerse themselves in local history and enjoy scenic train rides.
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 feature pools and hot tubs, making it an appealing destination for those seeking relaxation and leisure. This charming market town, located near the stunning North York Moors National Park, offers a range of properties that cater to various preferences. Travellers can expect amenities such as private, heated pools, outdoor hot tubs, and spacious gardens ideal for family gatherings or peaceful retreats. 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 140 options to choose from. This charming market town, located near the North York Moors National Park, offers a variety of accommodations that cater to travellers with pets. Many of these holiday rentals come equipped with essential amenities such as fully fitted kitchens, comfortable living spaces, and private gardens, making them ideal for families and groups. See all pet-friendly rentals in Pickering.
Are there any remote work holiday rentals in Pickering?
In Pickering, there are numerous holiday rentals suitable for remote work, with around 260 options available. This charming market town, located at the edge of the North York Moors National Park, offers a peaceful environment ideal for productivity. Many properties feature dedicated workspaces, such as desks and office areas, along with essential amenities like Wi-Fi to ensure a seamless working experience. 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 holiday rental amenities include complimentary Wi-Fi, fully equipped kitchens with cookware, dishware, and utensils, and often dishwashers for added convenience. Many properties also provide comfortable living areas, allowing guests to unwind after a day of exploring the nearby attractions, such as the picturesque North York Moors National Park and the charming Pickering Castle.
When is the best time to visit Pickering for a holiday rental?
The best time to visit Pickering for a holiday rental is during the peak season from July to September. This vibrant period draws countless visitors, eager to immerse themselves in the rich history, scenic landscapes, and local attractions. With the warm summer weather, typically ranging from 15 to 20 degrees Celsius, it's an ideal time to explore the charming streets, historic buildings, and the nearby North York Moors National Park.

July stands out as the most popular month, bustling with life and offering a diverse range of activities for travellers. You'll find everything from local festivals to outdoor events, creating a lively atmosphere that enhances your holiday experience. It's also a wonderful time for leisurely walks, picnics, and sightseeing, ensuring you can fully appreciate the picturesque surroundings.

If you're looking for a more cost-effective option, consider visiting in November. While this month is quieter, it offers a unique charm with fewer crowds and an opportunity to experience Pickering's beauty at a more leisurely pace. The autumn colours can be quite stunning, allowing for peaceful explorations of the area and its heritage.
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 immerse themselves in the charm of the North Yorkshire Moors. One of the top attractions is the Beck Isle Museum, which showcases local history and heritage through engaging exhibits. The picturesque Pickering Castle, a Norman fortress, offers a glimpse into the area's medieval past and stunning views of the surrounding landscape.

For those interested in the great outdoors, the nearby North York Moors National Park provides ample opportunities for walking, hiking, and exploring the natural beauty of the region, with trails suitable for all levels of fitness. The iconic North Yorkshire Moors Railway, which runs through Pickering, allows visitors to experience a nostalgic steam train journey through the scenic countryside, making it a popular attraction for families and railway enthusiasts alike.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.