
House vacation rentals in Pickering
Find and book unique houses on Airbnb
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.

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.
FamilyLocationAmenities

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!
LocationValueIndoor spaces

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.
FamilyLocationTV

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.
FamilyLocationTV

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.
LocationValueAccess

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.
ValueLocationTV

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.
ValueLocationGetting around

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.
FamilyLocationGetting around

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.
ValueLocationGetting around

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!
LocationFamilyBathroom

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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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.
FamilyValueIndoor spaces
Popular amenities for Pickering house rentals
House rentals with a pool

Willow cottage bungalow, pet friendly, heated pool
LocationFamilyParking

The Hideaway with Private Pool Sleeps 2
ValueFamilyBathroom

Silversands House at The Bay Filey - sea views
FamilyLocationPets

West End Farm
FamilyPetsPool

Lobster Pot Cottage The Bay - Filey
FamilyLocationComfort

Aubergine Cottage - Pool and Beach Access
FamilyLocationDecor

Salty Kisses, The Bay, Filey
FamilyValueKitchen

Brand new 2021 ABI WINDERMERE STATIC Cedar 1
LocationValueCheckout
Weekly house rentals

Spacious historic folly | family holidays | 6 BD
ValueFamilyGetting around

The Barn at Noelle's Cottages
FamilyLocationOutdoor spaces

The Tack Room Cottage Pickering
LocationTVAmenities

Little Fox Cottage
LocationWalkabilityPets

Summerfield Bungalow
LocationFamilyKitchen

Pottergate Lodge Helmsley | Hot Tub | Pets Welcome
FamilyValueComfort

Quiet Paradise Retreat for 4- near York and Whitby
LocationFamilyPets

Charming Yorkshire Cottage near The Coast & York
LocationDecorHospitality
Private house rentals

Relaxing Cosy retreat with Hot Tub under a canopy
ValueLocationQuiet

The Mill House, spacious barn conversion
FamilyLocationOutdoor spaces

Stylish retreat in Malton
LocationFamilyParking

Old Town Luxury, By The Sea - 3 en suite bedrooms.
LocationFamilyNearby

The Town House
LocationValueWalkability

Corner Cottage
LocationFamilyHeating

The Hideaway-with hot tub
ValueLocationGetting around

Family Farm Country Paradise -coast and country
LocationFamilyOutdoor spaces
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$35,098 GYD | G$35,725 GYD | G$32,382 GYD | G$36,560 GYD | G$36,560 GYD | G$34,680 GYD | G$43,037 GYD | G$40,739 GYD | G$39,485 GYD | G$36,143 GYD | G$38,859 GYD | G$39,694 GYD |
| 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
- Durham University
- Temple Newsam Park
- Royal Armouries Museum
- National Railway Museum
- York Minster
- Scarborough Beach
- Teesside University
- The Deep
- Bridlington Spa
- Peasholm Park
- First Direct Arena
- Blue Dolphin Holiday Park - Haven





