Holiday rentals in Pickering
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Quick stats about holiday rentals in Pickering
Total holiday rentals
Explore 160 holiday rentals in Pickering
Nightly prices starting at
Pickering holiday rentals start at £44 per night before taxes and fees
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Over 5,910 verified reviews to help you choose
Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
160 of Pickering holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pickering rentals
4.9 Average rating
Pickering stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated holiday rentals in Pickering
Guests agree: these stays are highly rated for location, cleanliness and more.
Cosy ‘Cobblers Cottage’ - Pickering
Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.
Cosy character cottage in heart of Pickering
31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.
Stationmaster's Cottage
A detached Victorian stone cottage in the shadow of Pickering Castle and overlooking North York Moors Railway station, this characterful property with real fire is only 3 minutes walk away from town centre amenities, the castle and a ten minute walk to the start of the Tabular Hills way and gateway to the North York Moors National Park. Free parking is provided in the Platform 3 Car Park diagonally opposite the property 70 yards away (dashboard pass provided). Please note: steep stepped access.
Spacious character historic cottage
Our 17th Century, characterful Yorkshire longhouse provides a spacious, retreat, and a fantastic base for family and friends to meet up with plenty of opportunities for days out in the surrounding North York Moors. The house is in the vibrant market town of Pickering with it's famous heritage railway. Pickering has a cafes, restaurants and pubs along it's bustling high street and a weekly market selling fresh, local produce. 7+2 guests (sofa bed in the snug for 2 guests at an extra charge)
Lovely cottage for N. York Moors & Steam Trains
19 Burgate is in the popular market town of Pickering, minutes’ walk from shops, eating places, Castle & Steam Railway (seasonal) - ideal for exploring the Moors, coastline & historic sights. It offers contemporary comfort, with a cosy living room, modern kitchen-diner, luxurious bathroom (walk-in shower, bath) & quality bedrooms. The garden offers eating/drinks outside and access to private parking. Prices are for 2 guests, with a small extra charge for the 2nd bedroom and well-behaved pets.
Cosy one bedroom cottage in Pickering
This lovely cottage is nestled in the centre of the beautiful market town of Pickering, Relax at this charming cottage which offers easy access to the enchanting landscapes of the North Yorkshire Moors and the nearby towns and coast. Whether you visit the iconic North Yorkshire Moors Railway, attend a concert at the Scarborough Open Air Theatre, or spend a day at the beach or exploring Whitby and the Moors. If you are seeking relaxation or adventure, this unique getaway is the perfect choice.
APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE
Detached holiday cottage Sleeps two (ONE DOUBLE BED) FREE WIFI Off road parking En-suite bathroom Fully equipped kitchen TV and fridge freezer Microwave Ideal location for all local attractions 2 minute walk into Pickering and local pubs, restaurants and shops Quotes from past guests: it's just perfect/best cottage we've stayed in/everything is so welcoming/ location is fantastic Places to visit in North Yorkshire http://www.iknow-yorkshire.co.uk/attractions/north_yorkshire/
Katiann's Cottage
Accommodation Master Bedroom, en-suite walk in shower, 1 x King Size Bed, Freeview TV Twin Bedroom - 2 single beds TV Travel cot & highchair available Bedlinen & Towels Bathroom - bath, shower, sink, toilet Kitchen Diner - dishwasher, Washer, electric oven & hob, fridge, microwave, cook utensils & iron Cosy lounge 2 leather recliner sofas, Smart TV, electric log burner Gas Central Heating Free Wi-fi 1 private parking space & plenty of free public parking & chargers nearby 1 x small dog fee
Stonedale Nook - Perfect Pad for Two
Based in the heart of Thornton-le-Dale within walking distance of all the local pubs, cafes, restaurants and shops, Stonedale Nook is a lovely one-bedroomed apartment that features high-end furnishings, generous double bedroom and all the conveniences of home. The result is a light, bright living space located in a picture-perfect village that's often described as Yorkshire's Little Gem. We are also a 5 minute walk from the very popular TV series, Bangers & Cash.
Castlegate Cottage
Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.
Beautifully renovated stable in Pickering
Brand new as of November 2022: The Hayloft on Eastgate is a former stable which has been newly converted and renovated into a cosy, well equipped holiday home situated in Pickering. The property sleeps up to 4 people and has everything you should need for a comfortable stay in this wonderful part of Yorkshire. The centre of Pickering, with its heritage railway, castle, eateries, shops and other amenities is a five minute walk away.
Old Forge in Wrelton, North Yorkshire.
This cottage, in the village of Wrelton near Pickering, was a 19th century blacksmith's forge and has now been renovated into a delightful living space complete with fully-equipped kitchen, large living room area, bathroom with walk-in shower and a cosy bedroom located on a mezzanine floor which is reached via a spiral staircase. The Old Forge offers a great location for a relaxing stay in beautiful North Yorkshire.
Popular amenities for Pickering holiday rentals
Stay near Pickering's top sights
Other great holiday rentals in Pickering
Tulip Cottage Pickering
La Fenetre Holiday Cottage
Beautiful Shepherds Hut in Private Garden
The Barn at Noelle's Cottages
Luxury Rural Cabin with Wood Fired Hot Tub
Exceptional Goathland House, West View Mews
Lovely Cottage & Garden. Family & Bike Friendly
Stunning views, 4 acres, dog friendly, Yorkshire
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £113 | £116 | £115 | £130 | £129 | £132 | £124 | £123 | £121 | £122 | £112 | £130 |
| Avg. temp | 3°C | 3°C | 5°C | 7°C | 10°C | 12°C | 15°C | 14°C | 12°C | 9°C | 6°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Pickering?
The town center area has character guesthouses, traditional cottages, and modern apartments, making it convenient for exploring markets, eateries, and historical sites on foot. Rural surroundings also include converted barns and countryside retreats for a quieter stay.
What are the best things to do in Pickering with kids?
Kids often enjoy exploring Pickering Castle, boarding the North Yorkshire Moors Railway for a steam train adventure, or playing in riverside parks. Farm visits and craft workshops are other frequently suggested options.
What are some of the best things to do in Pickering?
Explore Pickering Castle, ride the North Yorkshire Moors Railway, and visit the Beck Isle Museum for local heritage. Browsing markets, independent shops, and riverside walks reveals the area's character.
How is the weather in Pickering?
Pickering has cool, damp winters with highs near 41–46°F (5–8°C) and milder summers averaging 60–66°F (16–19°C). Waterproofs and layers are useful year-round, as rain is common across seasons.
When is the best time to visit Pickering?
Late spring through early autumn is often recommended for milder weather and seasonal events. Some visitors enjoy winter for quieter towns and festive markets, but packing for cooler temperatures around 33–42°F (1–6°C) is helpful.
What are the best places to visit in Pickering?
The most popular sites include Pickering Castle, the parish church with medieval wall paintings, and the North Yorkshire Moors Railway. Many guests also explore nearby forests and heather-clad moors.
What are some hiking trails in Pickering?
Explore woodland paths in Cropton Forest, gentle walks along Pickering Beck, or venture toward nearby moorland trails. These routes often feature scenic views and glimpses of local wildlife.
What are some family activities we can do in Pickering?
Families often explore Pickering Castle, join a steam train ride on the heritage railway, or enjoy interactive exhibits at local museums. Green spaces and adventure play areas also create opportunities for outdoor fun.
What are some of the best day trip ideas from Pickering?
Explore the historic city of York, beaches around the Yorkshire coast, or charming moorland villages known for walking and traditional markets. Nearby castles and ruins add to the variety of day excursions.
Are there any pet friendly accommodations available in Pickering?
Many accommodations in Pickering's countryside and town center welcome pets, especially in cottages, farm stays, and select apartments. Walking trails and pet-friendly cafes around Pickering make it easy to include pets in your plans.
What are some local tips for visiting Pickering?
Locals often suggest exploring smaller side streets for independent shops and sampling a traditional Yorkshire afternoon tea. Arriving early for market days or railway journeys can help you enjoy a quieter experience.
What is Pickering known for?
Pickering is known for its historic castle, heritage railway, and as a gateway to the North York Moors National Park. The town has roots in medieval history, markets, and railway traditions.
What are the best hidden gems to explore in Pickering?
Pickering has lesser-known corners, such as small local galleries, quiet riverside trails, and village tearooms with distinct character. Exploring independent antique shops and the town's market days unveils local traditions and crafts.
What are the best foods to try in Pickering?
Pickering has traditional Yorkshire treats such as pork pies, Wensleydale cheese, and hearty meat and vegetable pies. Seasonal cakes and local ales are often enjoyed in cafes and pubs around the town.
What should I bring for a trip to Pickering?
Bring layered clothing for shifting temperatures, waterproofs for rain, and comfortable walking shoes for uneven terrain. A camera helps capture the medieval architecture, steam trains, and moorland scenery.
What is the nightlife in Pickering like?
Pickering has a relaxed nightlife scene centered around traditional pubs, quiet lounges, and occasional live music in local inns. Most evenings are low-key, creating a welcoming atmosphere for conversation and sampling local ales.
What are the most popular events or festivals in Pickering?
Pickering hosts events like the wartime-themed 1940s Weekend, vintage car rallies, and seasonal fairs celebrating local traditions. Folk and craft festivals are also frequently suggested by residents and visitors.
Are there family friendly vacation rentals in Pickering?
Pickering's holiday cottages, barn conversions, and town center apartments frequently welcome families. Many rentals have amenities such as kitchens and enclosed gardens to support family needs during your stay.
All about Pickering
Lying at the southern border of the dramatic North York Moors, Pickering is an ancient market town that can trace its roots to 270 BCE. St Peter and St Paul’s church was built in Saxon times, and contains some of the country’s most complete medieval wall paintings; Pickering Castle was begun by William the Conqueror. You can still walk around the ruins of its motte-and-bailey fortress (used by no fewer than six English kings), while the Beck Isle Museum offers a chance to see everyday life as it’s been lived here in more recent centuries.
The town’s marketplace and high street are still the thriving hub of the community, full of independent shops, cafes, and businesses from bakeries to antique stores, while the natural splendour (and glorious isolation) of the moors are practically on the doorstep. And if that’s not enough to quicken your pulse, you can always visit the nearby theme park Flamingo Land.
What are the top things to do in Pickering?
Newbridge Park
Right below the towering stone walls of Pickering Castle sits this forested community park, whose woodland has been restored by local volunteers. It’s a great area for walking, and there’s also plenty here for mountain bikers, with cycle trails, a jump park, and a pump track. They’ve even turned a disused quarry into a pleasant picnic area.
North Yorkshire Moors Railway
This historic steam railway is one of the best in the country, and Pickering is its southern terminus. A ride along its 24-mile tracks will take you through beautiful Yorkshire countryside, where you’ll stop at a sequence of lovely villages, all the way to Whitby on the east coast. Even if you’re not planning a journey, it’s worth a visit to the station, whose vintage tearoom serves fresh pies and scones.
Kirk Theatre
There’s a real tradition of theatre-going in Pickering — the small town manages to maintain no fewer than three venues — and the Kirk is at its heart. Its home, a once-derelict Wesleyan chapel, is part of the town’s fascinating religious history as a centre for nonconformist believers in the 19th century, from Methodists to Quakers.
Destinations to explore
- Yorkshire Coast
- Filey Beach
- Flamingo Land Resort
- Durham Cathedral
- Bempton Cliffs
- Harewood House
- Fountains Abbey
- York Castle Museum
- Bramham Park
- Scarborough Open Air Theatre
- University of Leeds
- York University
- Durham University
- Temple Newsam Park
- Royal Armouries Museum
- National Railway Museum
- York Minster
- Scarborough Beach
- Teesside University
- The Deep
- Bridlington Spa
- Peasholm Park
- First Direct Arena
- Blue Dolphin Holiday Park - Haven