House vacation rentals in Pickering

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Quick stats about house rentals in Pickering

  • Total vacation rentals

    Explore 50 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at G$12,535 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 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!

Top-rated house rentals in Pickering

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

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Top guest favorite
Home in Welburn
4.98 out of 5 average rating, 123 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.

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Top guest favorite
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, 114 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!

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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, 143 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.

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Guest favorite
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, 132 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.

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Top guest favorite
Home in North Yorkshire
4.98 out of 5 average rating, 227 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.

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Top guest favorite
The exterior of a charming stone cottage is displayed, featuring a distinctive red pitched roof. Flower pots with blooming plants adorn the entrance. A well-maintained gravel pathway leads to the door, surrounded by lush greenery and shrubbery.
Home in Ampleforth
4.96 out of 5 average rating, 138 reviews

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to relax, listen to the wildlife and enjoy the beautiful countryside. The pretty market town Helmsley is less than 10 minutes drive, with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants. York is 45 mins drive and an hour to the coast for beach walks.

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Top guest favorite
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, 246 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.

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Top guest favorite
Home in Cloughton
4.99 out of 5 average rating, 103 reviews

Stylish spacious country cottage

Relax in this newly refurbished calm, stylish space, set in acres of land on our Victorian property within the North Yorkshire Moors National Park. We are perfectly situated for an active or relaxing break, located for coast and country. The Cedars will delight you with luxury furnishings ensuring, you have a relaxing and memorable stay. The stylish spacious living space is upstairs in order to take advantage of the beautiful uninterrupted views across open countryside to the sea.

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Guest favorite
An open-plan kitchen and living area features sleek cabinetry and contemporary lighting. Comfortable seating surrounds a wooden table, offering a space for dining or relaxation. Bi-fold doors open to a landscaped garden, allowing natural light to fill the room.
Home in Scarborough
4.86 out of 5 average rating, 406 reviews

Lovely semi/2xPubs/Open Air/Beach 5 min walk/Pets

Scholes Park by the sea is a beautiful semi detached home which sleeps 5 people minutes from the North bay beach by foot and the Scarborough open air theatre. Situated in a quiet reidential area yet still close to local amenities. With off street parking for several cars. The property has open plan living in a very contemporary style, a wood burner in the lounge making this very cosy. With rear bi-fold doors bringing the outside in. Front and back gardens both sun traps.

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Guest favorite
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, 204 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!

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Superhost
Home in North Yorkshire
4.88 out of 5 average rating, 159 reviews

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.

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Top guest favorite
An inviting upstairs lounge features a cozy sofa adorned with colorful cushions. A wooden coffee table sits on a textured rug. Natural light streams through the two windows, highlighting the exposed wooden beam above. A blue cabinet and a basket add warmth to the space.
Home in Hinderwell
4.97 out of 5 average rating, 111 reviews

The best views in Staithes?

A beautifully-presented, quirky cottage enjoying some of the best views in the village. Light and airy, it has been refurbished to a high standard - offering a stylish and cosy retreat in the heart of Staithes old town. It also has its own private garden. Guests love the stunning upstairs lounge, with uninterrupted views across the harbour. The cottage is warm and cosy, with electric heaters upstairs and underfloor heating and a log burner downstairs.

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Popular amenities for Pickering house rentals

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$35,098 GYDG$35,725 GYDG$32,382 GYDG$36,560 GYDG$36,560 GYDG$34,680 GYDG$43,037 GYDG$40,739 GYDG$39,485 GYDG$36,143 GYDG$38,859 GYDG$39,694 GYD
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