
House holiday rentals in Pickering
Find and book unique houses on Airbnb
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 $76 SGD per night before taxes and fees

Verified guest reviews
Over 1,190 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
50 of Pickering holiday rentals include wifi 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.

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!

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.

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. 1 minute walk to forest paths 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. Discounts for stays over 2 nights.

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.

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.

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.

Luxury 3 bedroom house - hot tub & amazing view!
Yoredale House is a stone-built 3 bedroomed detached property with amazing views set in its own grounds with a 5-person hot tub - just outside the beautiful village of Burton Leonard. Furnished to the highest standards with panoramic views towards the North Yorks Moors. Easy access to two National Parks, Fountains Abbey, Herriot country, Ripon, Harrogate, York etc. Two village pubs and shop within walking distance. Great base for walking, cycling and exploring beautiful North Yorkshire.

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.

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.

Oakforge Cottage, a spacious home from home.w
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.

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!

Saltburn Self Catering - Treetops
<p>This property is composed of a large open plan living space, balcony and kitchen on the ground floor. The lower ground floor includes two large bedrooms, two bathrooms and doors to an outside terrace space. Above the ground floor which includes seating and beautiful sea views. There is also a double sofa bed in the living room, allowing upto 6 guests. This property is dog friendly , there is an additional charge of £25 per stay.</p>
Popular amenities for house rentals in Pickering
House rentals with a pool

Cosy 2 bedroom river/coastal retreat. Heated pool.

Sandy Toes, The Bay, Filey

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

One bedroomed cottage with swimming pool.

The Hideaway with Private Pool Sleeps 2

West End Farm

Aubergine Cottage - Pool and Beach Access

Mill House - Birdforth Hall Holiday Cottages
Weekly house rentals

Spacious historic folly | family holidays | 6 BD

The Barn at Noelle's Cottages

The Tack Room Cottage Pickering

Swainsea Annex, Pickering

Pottergate Lodge Helmsley | Hot Tub & Pet Friendly

Hide Cottage with private parking

Quiet Paradise Retreat for 4- near York and Whitby

Vinery Farm - sleeps 10
Private house rentals

Family Farm Country Paradise -coast and country

The Mill House, spacious barn conversion

The Town House

The Hideaway-with hot tub

The Dovecote in Rosedale, NY

Sandfield House

Daisy Cottage - an enchanting cottage

Relaxing Cosy retreat with Hot Tub under a canopy
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $213 SGD | $217 SGD | $197 SGD | $222 SGD | $222 SGD | $211 SGD | $262 SGD | $248 SGD | $240 SGD | $220 SGD | $236 SGD | $241 SGD |
| Avg. temp | 3°C | 3°C | 5°C | 7°C | 10°C | 12°C | 15°C | 14°C | 12°C | 9°C | 6°C | 3°C |
Destinations to explore
- Yorkshire Coast
- Filey Beach
- Flamingo Land Resort
- Durham Cathedral
- Bempton Cliffs
- Harewood House
- Fountains Abbey
- York Castle Museum
- Bramham Park
- Scarborough Open Air Theatre
- University of Leeds
- York University
- Temple Newsam Park
- Durham University
- Royal Armouries Museum
- National Railway Museum
- York Minster
- Teesside University
- Scarborough Beach
- The Deep
- Peasholm Park
- Bridlington Spa
- First Direct Arena
- Blue Dolphin Holiday Park - Haven





