Vacation rentals in Pickering

4.96 out of 5 average rating, 134 reviews

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

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

Tiny home in North Yorkshire

A modern kitchen features sleek cabinetry with a vibrant teal backsplash. Open shelving displays carefully arranged dishware and plants. A black stove and kettle are positioned against the counter, with two bar stools inviting casual seating beside a window that offers natural light.

4.92 out of 5 average rating, 372 reviews

Diamond Den- a quiet, peaceful and private haven.

Situated in the extremely peaceful village of Butterwick, just a few moments walk to the river rye and bridge, Diamond Den is the perfect retreat. Being at the foot of the Howardian Hills provides a wealth of walking opportunities and we are just a short drive away from some spectacular market towns, including Helmsley (8m) Malton( 5.4m), Ampleforth (9.7m) and Pickering (8.5m). You will have your own private garden space and parking. ACCESS TO THE SLEEPING AREA IS UP A LADDER- PLEASE SEE IMAGES

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.

4.92 out of 5 average rating, 318 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.

The entrance to the barn features a charming wooden gate adorned with climbing plants, including wisteria and a yellow flowering vine. The pathway is lined with gravel, leading to the stone facade of the barn under a traditional red-tiled roof.

4.99 out of 5 average rating, 147 reviews

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

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.

4.93 out of 5 average rating, 130 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.

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.

4.84 out of 5 average rating, 164 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.

Place to stay in North Yorkshire

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.

4.86 out of 5 average rating, 186 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

Guest suite in North Yorkshire

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.

4.98 out of 5 average rating, 313 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.

Guest suite in Rosedale Abbey

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.

4.99 out of 5 average rating, 231 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.

4.97 out of 5 average rating, 233 reviews

A cozy workspace is depicted with a round wooden table and a comfortable chair. Shelves filled with books and decorative items line the walls. A small bouquet of flowers adds a touch of nature, while a warm-colored blanket drapes over another chair.

Tiny home in Heworth

York Poetree House, tiny treehouse home for one

Reconnect and wake up into nature at this unforgettable escape. Secluded treehouse with everything you need to soothe and inspire. Self cater, arrange meals provided by your host (a professional chef), or try one of the many eateries in town. Shops nearby. Your own private bathroom is situated a few yards away in the main house. You also can enjoy our beautiful garden, lily pond and friendly cat, Nina. Your hosts are always on hand to ensure a comfortable and nourishing experience.

4.93 out of 5 average rating, 268 reviews

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

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.

4.98 out of 5 average rating, 131 reviews

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

Maltkiln House Annexe North Yorkshire moors

Get away from it all, unplug and unwind. 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

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A space thats all yours, with room for everyone

Popular amenities for Pickering vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pickering

4.96 out of 5 average rating, 140 reviews

A bright living area features a blue sectional sofa with decorative pillows and a wooden coffee table. A wall-mounted TV is positioned above a contemporary electric fireplace. Large windows allow natural light to fill the space, and vaulted ceilings enhance the open feel.

Condo in North Yorkshire

Stylish apartment in the centre of Malton

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.

4.96 out of 5 average rating, 123 reviews

Spacious character historic cottage

4.98 out of 5 average rating, 286 reviews

Condo in North Yorkshire

Luxury boutique apartment-2 Chiltern Place Malton

The exterior of the cottage displays a charming stone facade with a red-tiled roof. A large window with multiple panes is positioned at the front, while two dormer windows are set into the roof, providing additional natural light to the upper levels.

4.93 out of 5 average rating, 377 reviews

Castlegate Cottage

5 out of 5 average rating, 143 reviews

A terrace features a round table set for two, accompanied by stylish woven chairs. A view of the lush green valley and surrounding trees creates a serene backdrop, while a small barbecue grill stands nearby on the stone surface.

Farm stay in Hartoft

Storey Corner - Where memories are made

Superhost

The exterior view of a charming two-story stone cottage is presented. A welcoming entrance with a white door is flanked by several windows. A small patio area includes seating and an umbrella, surrounded by landscaped greenery and flower beds.

4.84 out of 5 average rating, 115 reviews

Free Parking - Charming Country Cottage

Cottage in North York Moors National Park

Fields and rolling hills stretch into the distance under a clear sky, with scattered clouds casting soft shadows on the landscape. A wooden gate opens into the lush, green path leading towards open meadows, inviting exploration in the tranquil countryside.

4.99 out of 5 average rating, 571 reviews

Fully Fenced Dog Field, Sea Views & Autumn Walks