House holiday rentals in Pickering

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Quick stats about house rentals in Pickering

  • Total holiday rentals

    Explore 50 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Pickering holiday 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!

Top-rated house rentals in Pickering

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious, two-story house with white exterior walls is visible, showcasing multiple windows and a path leading to the front door. The sea is seen in the background, with a clear blue sky overhead, emphasizing the coastal location.
Home in North Yorkshire
4.97 out of 5 average rating, 101 reviews

Old Coastguard Station with Stunning Sea Views

The Old Coastguard Station sits overlooking Filey Bay and has stunning views of the sea from every room. A spacious and comfortable house, it provides an excellent base for families and couples alike, away from the bustle of the promenade, yet minutes walk to both the beach and town centre Sleeps 6 guests in three bedrooms An additional two guests can be accommodated on two fold up single beds. This is chargeable at £30 pp per night. A travel cot is available at £30 per stay Maximum 8 people

Top Guest favourite
Home in Welburn
4.97 out of 5 average rating, 107 reviews

Luxury Country Cottage Hot Tub Spa Retreat | York

Snowdrop Cottage is a luxurious 5★ retreat nestled in the picturesque village of Welburn, surrounded by the breathtaking Howardian Hills, just minutes from the iconic Castle Howard, the city of York and the Yorkshire coastline. An idyllic escape, this beautifully styled boutique cottage features a private garden spa & hot tub, cosy log burner & romantic four-poster king-size bed - the perfect setting for couples, families and dog walkers to relax, reconnect and explore the Yorkshire countryside.

Top Guest favourite
The cottage exterior features natural stone walls with a rustic charm. A red-tiled roof complements the warm tones of the facade. A spacious patio area includes wicker seating and a small table, ideal for outdoor relaxation. Nearby, greenery and trees provide a peaceful setting.
Home in Keldholme
5 out of 5 average rating, 104 reviews

Highfield Annex with off St Parking in Keldholme

Enjoy a tranquil getaway at Heather Annex! Explore the North York Moors by foot; cycle Dalby Forest’s trails or ride the iconic Pickering steam train to Whitby. Visit charming market towns like Helmsley and Kirkbymoorside. Nearby, discover TV's 'Bangers & Cash' or York. Coastal towns, Whitby & Scarborough are less than an hour away. Walk to local pubs and cafes. Return to 1/2 an acre of grounds featuring American Miniature Horses & hens. Or simply unwind on the Patio & have a peaceful stay!

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
4.98 out of 5 average rating, 127 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 sunroom features wooden walls and flooring, complemented by a cozy seating arrangement with two chairs and a small table. Decorative plants adorn a shelving unit, and cushions add a touch of color. A neutral-toned rug extends across the floor, enhancing the inviting space.
Home in North Yorkshire
4.95 out of 5 average rating, 115 reviews

The Sanctuary, Pet friendly

Relax with the whole family at this peaceful place to stay. Beautiful village residence but only 4 miles from stunning historic York with easy public transport access. Bring your pet too, they have indoor and outdoor space and wonderful country walks in the local area. Enjoy our sunroom, a cosy space to eat in Summer or Autumn. Our local pub is on the doorstep serving excellent home cooked meals or a take away Sunday lunch. With 2 parking spaces and secure lock up lock up for mountain bikes.

Top Guest favourite
Home in North Yorkshire
4.98 out of 5 average rating, 211 reviews

Gorgeous country cottage, Nawton near Helmsley

A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

Top Guest favourite
Home in Wilberfoss
5 out of 5 average rating, 131 reviews

The Nest with Luxury Hot Tub

We are proud to list our second property, 'The Nest’. A brick built detached cottage with rustic modern farmhouse design a comfortable home from home experience, ideal for romantic getaways. Our luxury accommodation features cosy open plan lounge/dining area with feature brick walls with French doors leading to a private walled patio area with luxury state of the art 6-seater hot tub for your sole use, fully fitted kitchen, luxurious bathroom, elegant, panelled bedroom with king sized bed.

Guest favourite
The exterior of a historic house displays its charming brick facade, highlighted by tall gothic windows and a distinctive turret. Surrounded by well-maintained lawns, benches invite relaxation under the clear blue sky, enhancing the serene setting.
Home in Wintringham
4.93 out of 5 average rating, 114 reviews

Spacious historic folly | family holidays | 6 BD

If you're looking for a break with family or friends in North Yorkshire, let's talk. Deer Park is a much loved house with a long history. Today it is a comfortable base for a break with as much adventure, relaxation, romance and celebration as you might want. Set in 20 acres of Capability Brown parkland the house sleeps 10 people, in 6 bedrooms and 3 bathrooms, with a huge kitchen diner and 4 more reception rooms. Dogs are welcome! Less than 30 minutes to York, the coast and the moors.

Top Guest favourite
A wide expanse of golden fields stretches towards the horizon, framed by a wooden fence. Lush greenery and tall grasses populate the foreground, while patches of blue sky and scattered clouds fill the background, reflecting the tranquil beauty of the surrounding countryside.
Home in North Yorkshire
4.98 out of 5 average rating, 129 reviews

Summerfield Bungalow

Summerfield bungalow is located just outside the village of Hawsker, midway between Whitby & Robin Hood’s bay. The bungalow is private, detached, not overlooked & is spacious, bright with stunning views from every window. From the front you can see Whitby Abbey and harbour, from the side there’s a lovely view of All Saints church approx 20 metres away & from the rear there are uninterrupted views of the Yorkshire countryside. The gardens extend to around a third of an acre and are secure.

Top Guest favourite
A steam train is seen departing from a vintage railway station, with wisps of steam billowing from the engine. The station's platform is surrounded by greenery, and classic signal lights are positioned along the tracks, enhancing the historical ambiance.
Home in North Yorkshire
4.89 out of 5 average rating, 234 reviews

Short stroll to pubs, cafés & shops. Free Parking

Enjoy a clean and comfortable, cosy yet spacious, experience at this peacefully located holiday home. Just a very short stroll from Pickering town centre where you’ll be spoilt for choice 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 or free parking permit for Eastgate car park which is less than 300 meters away.

Guest favourite
A bright bedroom features a spacious bed with soft bedding, complemented by a decorative chest of drawers. Natural light floods the room, highlighting the neutral decor. A doorway leads to an en-suite bathroom, and a comfortable seating area is visible in the background.
Home in Kirkbymoorside
4.9 out of 5 average rating, 459 reviews

Oakforge Cottage, a spacious home from home.

Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.

Guest favourite
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
4.92 out of 5 average rating, 197 reviews

Luxury one bedroom cottage with log burning hot tu

Relax and unwind in the newly refurbished one bed Irishman's Cottage. The cottage retains many old features and is surrounded by the rolling hills of the Yorkshire Wolds. The living space is open plan with ample space for a couples retreat or family break away. In the summer months dine al fresco and enjoy a BBQ on the private patio besides the wood burning hot tub. A short walk away is our private lake, where you might catch site of a resting deer or hare!

Popular amenities for Pickering house rentals

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