Holiday houses in Pickering

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Top-rated holiday rentals in Pickering

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Cottage in North Yorkshire
4.92 out of 5 average rating, 336 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, 111 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
The exterior of a characterful Yorkshire longhouse is displayed, showcasing stone walls and a tiled roof. Flower baskets hang from the front, adding a touch of color. The entrance features a light-colored door framed by two potted plants. Windows reflect a welcoming ambiance.
Cottage in North Yorkshire
4.96 out of 5 average rating, 124 reviews

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)

Top Guest favourite
The exterior of a charming stone cottage is visible, featuring a traditional roof with red tiles. Two entrances can be seen, framed by multiple windows that allow natural light to enter. The facade combines a rustic aesthetic with neighborhood characteristics.
Cottage in North Yorkshire
4.94 out of 5 average rating, 140 reviews

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.

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 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, 350 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
Three modern bed sheds are presented, featuring sleek lines and triangular roofs. Soft lighting highlights the wooden exteriors, creating a warm ambiance. A wooden fence offers privacy while trees stand in the background, contributing to the serene countryside setting as dusk approaches.
Place to stay in York
4.97 out of 5 average rating, 116 reviews

The Helmsley -en-suite, king bed, great views

The bedsheds are modern in design, offering little luxuries throughout. We have thought of your every need for a great escape for two!. If you’re looking for somewhere to spend time, relaxing with lovely views or to explore the amazing attractions in North Yorkshire, we’re in a great location to do both. With heating and log burners we are able to offer cosy breaks all year round. A great space for romantic Escape, friends get away or work! We can’t accommodate Children/ infants Dogs/pets

Top Guest favourite
Place to stay in North Yorkshire
4.87 out of 5 average rating, 203 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, 168 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, 291 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.

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, 333 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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Avg. price$247 NZD$241 NZD$241 NZD$269 NZD$278 NZD$285 NZD$292 NZD$288 NZD$283 NZD$243 NZD$245 NZD$252 NZD
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Frequently Asked Questions

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

    Experience the best of Pickering with our cabin rentals, starting at about $240 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.

  • 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 cabin rentals in Pickering have a kitchen?

    Absolutely! We offer over 10 cabin rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pickering have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Pickering?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 40 homes with free parking, over 60 homes with wifi, over 60 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly cottage rentals in Pickering?

    Pickering has more than 60 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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 $87 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Pickering holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Pickering rentals

  • 4.9 Average rating

    Pickering stays are highly rated by guests—averaging 4.9 out of 5!

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  5. Pickering