Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

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Top guest favourite
Cottage in North Yorkshire
4.92 out of 5 average rating, 338 reviews

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.

Top guest favourite
A spacious living area features a green sectional sofa and a complimentary armchair. A coffee table is centered on a woven rug, with a decorative ladder parallel to a shelf adorned with plants. Large windows allow ample natural light, framed by green accents.
Home in North Yorkshire
4.97 out of 5 average rating, 107 reviews

The Bothy

Adults only/no pets..our Ethos ..to make your visit relaxing, recharge your batteries, revisit..all in a peaceful setting but don’t take our word for it..read our Reviews! We may not have cooking facilities but Pickering has some great eateries and pubs…what we do have is a kettle/coffee machine/fridge/BBQ Discounts for sun-thurs and early bookings…don’t delay book today! Come to beautiful North Yorkshire so much to see and do you may never want to leave! A warm welcome awaits you at The Bothy

Top guest favourite
A charming Victorian stone cottage stands against a backdrop of greenery. The cottage features a mix of dark stone and light brick, with a small front porch and a sloped garden area. Two large windows allow natural light to enter the welcoming interior.
Home in North Yorkshire
4.97 out of 5 average rating, 113 reviews

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.

Top guest favourite
A snug lounge area is shown with a sofa adorned with colorful cushions, a wooden TV stand below a flat-screen television, and soft lighting creating a welcoming ambiance. Stairs lead to an upper level, accompanied by decorative elements on the walls.
Cottage in North Yorkshire
4.84 out of 5 average rating, 175 reviews

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.

Top guest favourite
A charming building features wooden siding and large windows that illuminate the interior. Surrounding the structure is a well-kept garden with diverse greenery and pathways, enhancing the outdoor ambiance. The picturesque setting is complemented by a stone patio area for sitting and relaxing.
Guest suite in North Yorkshire
4.98 out of 5 average rating, 333 reviews

*The Vicarage Annexe, Carlton, North Yorks 1BR S/C

The Vicarage Annexe is a beautiful, one double-bedroom facility situated at the foot of the Cleveland Hills. The building was originally built as a prayer and study room for the Vicarage. This is now a self-contained living area with en-suite facilities. The Annexe is located in the picturesque village of Carlton-in-Cleveland, which is in the North Yorkshire Moors National Park and this is an ideal location for a couple who enjoy the countryside for relaxing, sightseeing, walking or cycling.

Top guest favourite
A detached holiday cottage features a red front door and distinctive round window, set against a backdrop of textured brick walls. The surrounding area is landscaped with greenery, and gravel provides off-road parking in front of the building.
Cottage in North Yorkshire
4.93 out of 5 average rating, 351 reviews

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/

Top guest favourite
The living kitchen area features exposed beams and floral wallpaper. A cozy seating arrangement is complemented by a plush rug and a vintage cast iron stove. Kitchen amenities are visible, including a stove, oven, and storage. Warm light fixtures illuminate the space.
Guest suite in Rosedale Abbey
4.99 out of 5 average rating, 246 reviews

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Top guest favourite
Place to stay in North Yorkshire
4.87 out of 5 average rating, 204 reviews

Strolling Distance To Town Centre-Car Parking INC

Enjoy a clean, comfortable, experience at this peacefully located, budget friendly holiday home. Just a very short stroll away from Pickering town centre with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking subject to availability or car park with ev chargers less than 300 meters away. Free parking permit included

Top guest favourite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny home in Urra
4.98 out of 5 average rating, 170 reviews

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annex is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Top guest favourite
The living area features a cozy sofa covered with a soft grey throw, complemented by patterned cushions. A wooden dining table is visible nearby. Stone walls and exposed wooden beams create a charming, rustic feel, while a wood-burning stove adds warmth to the space.
Barn in North Yorkshire
4.92 out of 5 average rating, 295 reviews

Delightful Barn with log burner near Pickering

A tranquil, 19th century converted barn with private garden and outdoor fire overlooking the local countryside. A short drive from Pickering and close to the Moors, Whitby and York, the barn is great for a relaxing break. Inside, you will find a renovated living area, with a wood burning stove, Smart TV and fully fitted kitchen complete with oven, fridge washing machine and dish washer, the barn offers everything you will need for a relaxing getaway in Yorkshire.

Top guest favourite
The open plan living area features a log burner surrounded by a brick fireplace, complemented by a comfortable blue chair and a coffee table. A dining area with a wooden table is visible in the background, while a fully equipped kitchen is accessed through an archway.
Cottage in North Yorkshire
4.94 out of 5 average rating, 104 reviews

2 bed Cottage Pickering, Priv Parking, Logburner

Oak Cottage is in the perfect place to explore Pickering and the surrounding North Yorkshire Moors and Coast. With Parking for 1 car and Just a 5 to 10 minute walk into central Pickering and the NYM Railway. Fully equipped for a comfortable and relaxing stay with lots of luxurious extras. We can sleep upto 4 people and one well behaved dog is welcome, but must be added to your booking for a small charge. It is a terraced cottage on the main road.

Guest favourite
A large floor-to-ceiling window offers expansive views of the countryside and sunlight filtering through trees. A warm wooden bench is adorned with a welcoming sign and small plants. A cozy coffee table with decorative items can be seen in front, enhancing the inviting space.
Barn in Aislaby, Pickering
4.95 out of 5 average rating, 335 reviews

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Pickering?

    Experience the best of Pickering with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Pickering?

    Yes! Work meets play with ease at over 10 house rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What types of vacation rentals are available in Pickering?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Pickering. From over 40 house rentals to over 70 cottage rentals, we've got you covered.

  • Do cottage rentals in Pickering have wifi?

    Absolutely! We offer over 60 cottage rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly cottage rentals in Pickering?

    Four-legged friends are welcome in Pickering. Choose from more than 30 cottage rentals for guests traveling with pets.

  • Do house rentals in Pickering have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Pickering have free parking?

    Absolutely! We offer over 40 cottage rentals with free parking in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Pickering?

    Pickering has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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.

Quick stats about holiday rentals in Pickering

  • Total holiday rentals

    Explore 150 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 4,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 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

    150 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!

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Pickering