Vacation rentals in Pickering

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Top-rated vacation rentals in Pickering

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

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Top guest favorite
A converted stable features a quaint exterior with a terracotta tiled roof and green door. Surrounding the building, a garden displays various flowers and plants, while a gravel path leads to the entrance. Mature trees provide shade, enhancing the outdoor space.
Barn in Scagglethorpe
4.97 out of 5 average rating, 154 reviews

Cosy Stable in Scagglethorpe

Ancient listed stable in Viking village, recently converted to the highest standards. Take a drink and enjoy your patio, explore the garden or amble down to the village pub for dinner or breakfast. Your own driveway parking space and a type2 EV charger. Relax in your kingsize bed, or unwind in the rainfall shower after a busy day visiting Castle Howard, Scampston Hall, Sledmere House, the coast, York, or wandering the Moors. Kettle and toaster (no oven), fridge, TV and high-speed WiFi provided.

Guest favorite
A traditional stone cottage features a charming entryway adorned with climbing plants. A small outdoor seating area, furnished with a round table and decorative chairs, provides a pleasant space for relaxation. The roof is covered with terracotta tiles, complementing the natural stone exterior.
Cottage in Pickering
4.96 out of 5 average rating, 135 reviews

Mill Cottage Is A Beautiful Cosy Country Escape

Escape to the country to the beautiful Moors Market town of Pickering.Just a short stroll from the centre of town lies Mill Cottage.A traditional country cottage furnished to the highest standard with a modern twist. With direct access to some of the most outstanding walks in the Moors but a fantastic convenient location for the amazing selection of country pubs , restaurants and attractions Pickering has to offer. The greatest care is taken to ensure your stay with us is as perfect as possible

Top guest favorite
The cottage is constructed of traditional stone, showcasing a quaint exterior with a pitched roof and chimney. Two large windows with flower boxes frame the entrance, which features a light-colored door. The surroundings include a peaceful street lined with other characterful buildings.
Cottage in North Yorkshire
4.92 out of 5 average rating, 327 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 favorite
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, 104 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 favorite
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, 104 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.

Guest favorite
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
4.93 out of 5 average rating, 134 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.

Guest favorite
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, 167 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.

Guest favorite
A dining area is visible below, featuring a glass table set for two with plates and utensils. Two elegant chairs frame the setting, complemented by a nearby decorated Christmas tree. Exposed wooden beams above add character to the space, enhancing the modern design.
Place to stay in North Yorkshire
4.87 out of 5 average rating, 194 reviews

Strolling Distance To Pickering Town Centre

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. Secure garage for bikes and/or motorcycles

Top guest favorite
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
4.92 out of 5 average rating, 343 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 favorite
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, 237 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.

Guest favorite
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, 277 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 favorite
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, 323 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 vacation rentals

When is the best time to visit Pickering?

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Avg. priceG$29,706 GYDG$29,078 GYDG$29,078 GYDG$32,425 GYDG$33,471 GYDG$34,308 GYDG$33,053 GYDG$35,145 GYDG$33,889 GYDG$29,287 GYDG$29,496 GYDG$30,333 GYD
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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 $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Work meets play with ease at over 40 cottage rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 40 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Pickering have wifi?

    Absolutely! We offer over 40 house 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 cottage rentals in Pickering have a kitchen?

    Absolutely! We offer over 60 cottage 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.

  • Are there family-friendly cottage rentals in Pickering?

    Pickering has more than 50 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Pickering

  • Total vacation rentals

    Explore 150 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at G$10,460 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Pickering vacation rentals include wi-fi 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!

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  5. Pickering