Family-friendly vacation rentals in Pickering

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, 329 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.

4.97 out of 5 average rating, 104 reviews

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

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

4.97 out of 5 average rating, 107 reviews

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

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 suite in Nunnington

A cozy suite is featured, with a spacious bed neatly made. A comfortable seating area contains a gray sofa with decorative pillows, a vintage trunk, and a piano. Natural light pours through two windows, illuminating the wooden floor and soft wall colors.

4.87 out of 5 average rating, 204 reviews

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

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, 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.

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, 168 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.

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.

4.92 out of 5 average rating, 345 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/

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.

4.87 out of 5 average rating, 196 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

4.9 out of 5 average rating, 129 reviews

A view of tranquil rooftops showcasing the unique character of the surrounding buildings with a mix of red brick and tile. Lush greenery and trees provide a soft backdrop, highlighting the natural beauty found in this serene rural area.

Home in North Yorkshire

Country Cottage with Steam Railway Views

Positioned on a pedestrian road, wake up to the sound of birds or the steam railway. Cosy up to the log burner or sit out in the evening sun, on our west facing decking overlooking the railway. A 1 minute walk to forest walks and Pickering castle, or a 2 minute walk to the town centre; you couldn’t be more perfectly located. Pickering has the charm of a rural North Yorkshire town with all the amenities you need for a relaxing break or a family centred vacation.

4.98 out of 5 average rating, 152 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 Annex 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.

Barn in Aislaby, Pickering

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.

4.95 out of 5 average rating, 327 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.

A welcoming living space features a brick fireplace with an activelog burner, offering warmth to the room. A comfortable futon sofa is accompanied by soft pillows, while a wooden coffee table sits on a woven area rug. A wall-mounted TV is visible above a modern radiator.

4.98 out of 5 average rating, 111 reviews

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.

Popular amenities for Pickering family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 172 reviews

An elegant freestanding bathtub sits against a rustic stone wall featuring exposed wooden beams. A potted plant is positioned nearby, adding a touch of greenery to the serene setting. The smooth tile floor enhances the bathroom's spacious feel.

Home in Malton

Luxury one bedroom cottage with log burning hot tu

An outdoor courtyard is presented with a hot tub, framed by greenery and stone walls. A wooden table holding a teapot and cups adds a cozy touch. Decorative elements like pinecones and flowers enhance the space, inviting relaxation in this private setting.

4.83 out of 5 average rating, 484 reviews

La Fenetre Holiday Cottage

Shepherd’s hut in North Yorkshire

The interior features a warm wooden design with natural light streaming through multiple windows. A sumptuous king-size bed is prominently placed, while a freestanding copper roll-top bath adds a touch of luxury. Decorative artwork and pendant lighting complement the tranquil space.

4.97 out of 5 average rating, 638 reviews

Stunning rural shepherds hut

4.97 out of 5 average rating, 912 reviews

A shaded outdoor dining area features a long wooden table with benches, surrounded by greenery. A fire pit with seating is positioned nearby, with the open countryside visible in the background. Sunlight casts gentle shadows across the gravel patio and lawn.

Shepherd’s hut in York

The Hut in the Wild

4.91 out of 5 average rating, 169 reviews

A hot tub is positioned on a paved area, surrounded by gravel and wooden fencing. Lush greenery is visible in the background, with a cloud of steam rising from a passing steam locomotive, creating a unique view. Outdoor seating can be seen nearby.

Cottage in Newbridge

3 Railway Cottage Pickering , Hot Tub, Pets all'd

Cottage in Newton-on-Rawcliffe

A stone cottage with a red-tiled roof is visible behind a dry-stone wall. Brightly colored flowers and greenery surround a playful pig statue in the foreground. The sunny sky provides a clear view of the welcoming farmhouse and its charming surroundings.

4.98 out of 5 average rating, 186 reviews

Charming farm based cottage with hot tub/sauna

4.98 out of 5 average rating, 316 reviews

A wooden balcony extends from the cabin, surrounded by lush greenery and tall oak trees. Sunlight filters through the leaves, creating a serene and natural ambiance. The dense forest provides a sense of seclusion, enhancing the retreat's peaceful atmosphere among the treetops.

Hut in North Yorkshire

Crumbleclive Cabin

4.95 out of 5 average rating, 125 reviews

A gravel pathway leads gently through a lush green lawn towards 'The Highlander' pod, framed by trees and bushes. Soft lighting fixtures line the pathway, guiding guests to the entrance of the cabin, nestled in a serene natural setting.

Cabin in Ugthorpe

The Highlander

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 160 reviews

The open-plan space features a spacious bed with plush bedding and two leather armchairs positioned beside a wooden dining table. Natural light enters through a window with checked curtains, creating a cozy ambiance. A flat-screen TV is mounted on the wall nearby.

Guesthouse in Kilburn

The Little House Peaceful & self-contained

4.99 out of 5 average rating, 529 reviews

The exterior of the building is showcased, featuring stone walls and a traditional red tile roof. Windows are framed in white, reflecting a classic style. A small bench is visible near the entrance, and a stone wall borders the pathway leading to the welcoming entrance.

Cottage in Danby

Farm Cottage with Stunning Views.

4.98 out of 5 average rating, 386 reviews

A light blue beach house is featured, set against a clear blue sky. A spacious deck is adorned with a white umbrella, while a comfortable seating area invites relaxation. Lush green grass surrounds the property, contributing to a cheerful outdoor setting.

Cabin in Filey

Secret of Eden Beach House - Pet friendly WiFi E.V

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, 379 reviews

Castlegate Cottage

Cottage in Kirkbymoorside

A comfortable lounge area features a pink sofa, a red chair, and wooden flooring. A staircase with wooden banisters leads to the upper level. A dining table with white chairs sits in the background, complemented by a simple wall decoration and a standing lamp.

4.87 out of 5 average rating, 460 reviews

Fuchsia Cottage- a cosy getaway

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, 582 reviews

Fully Fenced Dog Field, Sea Views & Forest Walks

Apartment in North Yorkshire

A tastefully decorated bedroom features a spacious bed with high-quality linen and pillows. A green accent wall enriches the space, complemented by framed art. A wall-mounted TV is visible, alongside a bedside table and lamp. Natural light streams in through a window dressed with blinds.

4.97 out of 5 average rating, 139 reviews

Esplanade Escape. Newly renovated, prime location

4.99 out of 5 average rating, 128 reviews

The image displays three modern BedSheds with distinctive gabled roofs, gently illuminated by exterior lights. A wooden fence runs along the front, providing a sense of privacy. Surrounding trees create a natural backdrop, enhancing the tranquil environment.

Place to stay in York

The Hovingham - en-suite, king bed & great views

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 103 reviews

The exterior of a two-story brick cottage is presented, showcasing a modern architecture with white window trims. A well-maintained lawn and hedges frame the property, while a clear blue sky with scattered clouds provides a bright backdrop.

Cottage in Filey

Willow Cottage: 3 Bed, 3 Bath, Pool, WiFi, dogs

4.86 out of 5 average rating, 110 reviews

The spacious living area features two plush sofas adorned with decorative cushions, positioned around a central glass coffee table. A contemporary lamp stands beside a window, allowing natural light to brighten the modern décor, with a geometric rug adding subtle texture to the space.

Apartment in Langton

Jubilee Hall apartment 2 - Modern and spacious

4.94 out of 5 average rating, 160 reviews

The charming cottage exterior features a warm brick facade with a green front door. Several windows offer natural light, surrounded by low-maintenance landscaped gardens with a variety of plants. The building's roof is lined with traditional tiles, creating a cozy neighborhood atmosphere.

Home in The Bay

Sandy Toes, The Bay, Filey

Cottage in The Bay North Yorkshire

The exterior of Collie Cottage is presented, showcasing a welcoming entrance with a well-maintained pathway. A stylish sign displays the street name 'Seaford Avenue.' The brick façade is complemented by traditional windows and a neatly trimmed lawn, reflecting a relaxed coastal charm.

4.98 out of 5 average rating, 189 reviews

Relax at lovely Collie Cottage, The Bay Filey

4.97 out of 5 average rating, 112 reviews

The living area features a blue sofa, a brown leather chair, and a patterned area rug with colorful accents. A wooden dining table and storage units with books and decorative items are positioned throughout. Light enters through large windows, complemented by a television in the corner.

Place to stay in York

Hot Tub Pet Friendly York

4.92 out of 5 average rating, 190 reviews

An open plan living area showcases a modern kitchen with stainless steel appliances and wooden cabinetry. A cozy leather sofa and a light wood coffee table with a decorative plant arrangement create a relaxed atmosphere. Brightness is provided by overhead lighting and natural light from a nearby window.

Condo in North Yorkshire

Yorkshire Coast Retreat The Bay Filey Wifi Pets

Superhost

A modern caravan is set against a cloudy sky, featuring a spacious deck with a railing. Large glass doors provide access to the outdoor space, and the exterior is complemented by warm lighting. Lush green grass surrounds the caravan.

Home in Cayton Bay

4.88 out of 5 average rating, 147 reviews

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