Holiday rentals and lettings in Pickering

Table of contents

• At a glance: what should you know about renting a holiday rental in Pickering?
• Holiday rentals in Pickering: find your perfect retreat
• Exploring Pickering: our top recommendations
• Activities: what are the top things to do and see in Pickering?

• Diverse accommodation options: Character-packed cottages, barn conversions, and town-centre apartments are available. You'll find everything from cosy two-person retreats to spacious properties sleeping up to twelve guests comfortably.
• Essential modern amenities: Woodburners, full kitchens, enclosed gardens, Wi-Fi, and private parking are included in most properties, ensuring comfortable self-catering stays throughout your visit.
• Neighbourhoods to suit everyone: Town centre location offers instant access to Pickering Castle and attractions, while Moors Gateway provides direct access to North York Moors National Park walks.
• Family-friendly focus: Many properties feature cots, highchairs, children's play areas, and bike storage, with bed linen and towels included for hassle-free arrival.
• Highly praised by guests: Properties receive great reviews for historic charm, peaceful enclosed gardens, and ideal positioning for exploring both Yorkshire Moors and coastal destinations.

Pickering offers a delightful range of traditional character cottages, barn conversions, and town-centre apartments suited to all visitors. There's a holiday home to suit every group. Look out for amenities such as:

• Open fires, woodburners, and log burners
• Fully-equipped kitchens
• Enclosed gardens or patios
• Designated parking

As well as cosy cabins and modern apartments, consider glamping in Pickering for a quirky, unusual holiday you're bound to remember.

What are the best areas to stay in Pickering?

Pickering town centre remains the most popular location, offering immediate access to local attractions, independent shops, and restaurants whilst staying within a charming historic setting. The table below details areas for specific interests:

Pickering's holiday rentals consistently earn praise for their combination of historic character and modern comfort. Guests particularly highlight the cosy woodburner atmospheres, peaceful enclosed gardens, and the town's ideal positioning for exploring both the North York Moors and Yorkshire coast. Here are some of our top-rated properties from the last year:

Apartment 'Station View' with parking- 9.7+: This charming two-person apartment is just right for a couple in search of peace and quiet. Guests love the central location.
1. Cottage 'Westgate' with garden - 9.6+: With room for four, this lovely stone cottage receives great reviews for its spotless interior and homely feel.
2. Cottage with fireplace and garden - 9.8+: This five-person cottage dates back to the 17th century. Guests love its charming period décor and praise the dog-friendly atmosphere.

Nestled at the edge of the North York Moors National Park in North Yorkshire, Pickering is a charming market town renowned as the gateway to the moors, offering visitors the perfect blend of countryside tranquility and easy access to coastal delights.

✈️What is the best way to get to Pickering?

Pickering is a compact market town, easily walkable once you arrive, with a car most useful for exploring the wider Moors and coast. Here are the most common ways to get there:

• By car: It takes about 2 hours to drive from Manchester to Pickering, along the M62 and A64.
• By train: Pickering is reachable by train via nearby Whitby, or the heritage North Yorkshire Moors Railway from Grosmont.
• By air: The closest major airport is Teesside International, around 52 miles or a 1 hour 15 minute drive away, with car hire available on-site.

🍴Where to eat in Pickering?

According to Google Maps data and reviews, Willowgate Bistro is the best rated restaurant in Pickering. Below is a table showing the top 5 highly-rated restaurants hand-picked by our travel experts.

⭐Our guests' recommendation: Our guest traveller James recommends Cedar Barn Farm Shop and Café in Pickering: this award-winning farm shop café grows and sources nearly everything on-site or from across North Yorkshire, and is famous locally for its ploughman's lunches and Sunday roasts.

☀️When is the best time to visit?

The best time to visit Pickering is late summer (August into September), when the North York Moors turn purple with heather in full bloom.

Summer (June–September)

• Best for: Heather in full bloom across the North York Moors, especially late summer into September.
• Weather: Mild to warm, with generally the driest and sunniest conditions of the year.
• Atmosphere: Lively, with visitors drawn to the moors and town centre.

Winter (November–March)

• Best for: Cosy pubs and woodburning fires in many of the town's cottages, and good value for money.
• Weather: Cold, with shorter days and a higher chance of rain.
• Atmosphere: Peaceful, with the heritage North Yorkshire Moors Railway running extra festive services around Christmas.

Shoulder season (April–May and September–October)

• Best for: Quieter, cooler walking weather on the Moors.
• Weather: Mild and changeable, with fewer extremes than summer or winter.
• Atmosphere: Relaxed and considerably quieter than the summer months.

⭐Our hosts' recommendation: Our local Pickering hosts recommend visiting in September for the chance to enjoy the North Yorkshire Moors Railway Steam Gala. As well as vintage locomotives, the celebration includes a real ale beer festival and a number of other fun events for young and old.

1. Explore Pickering Castle
2. Learn local history at Beck Isle Museum
3. Admire the wall paintings at St Peter and St Paul's Church
4. Ride the North Yorkshire Moors Railway
5. Walk or cycle in Dalby Forest

1. Explore Pickering Castle

   Built by the Normans in 1069, these vibrant green castle grounds include ruined towers, an old chapel, and informational plaques, with spectacular views over the town.

2. Learn local history at Beck Isle Museum

   This well-organised museum spans 27 display areas covering Pickering's culture and heritage through plaques, artworks, and artefacts.

3. Admire the wall paintings at St Peter and St Paul's Church

   This medieval church in the town centre holds one of the most complete sets of 15th-century wall paintings in England.

4. Ride the North Yorkshire Moors Railway

   Climb aboard a 1930s-style steam locomotive for a scenic 24-mile journey through the Moors, with a food menu available on board.

5. Walk or cycle in Dalby Forest

   This expansive forest just outside town offers waymarked trails for walking, mountain biking, and wildlife spotting.