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Vacation rentals in Pickering

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Top-rated vacation rentals in Pickering

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

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Cottage in North Yorkshire

4.78 out of 5 average rating, 161 reviews

Cosy ‘Cobblers Cottage’ - Pickering

Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.

Nov 8 – 15

R2,249 ZAR per night

Cottage in North Yorkshire

4.96 out of 5 average rating, 95 reviews

Drapers Cottage, Pickering, sleeps 4, dog friendly

Lovely old Grade II listed stone cottage with exposed beams, open fire & courtyard garden. Sleeps 4: 1x large double bedroom & 1x small room with 2 singles. Bathroom & 2 toilets. Suitable for couples & families with older children. Not suitable for small children/toddlers or those less steady on their feet. Dog-friendly. Parking usually possible for one car outside cottage - additional free parking nearby. Wi-fi, smart TV, dishwasher, washing machine. Bikes can be kept in rear courtyard.

Jun 15 – 22

R2,258 ZAR per night

Cottage in North Yorkshire

4.91 out of 5 average rating, 250 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/

Mar 3 – 10

R1,945 ZAR per night

Barn in Aislaby, Pickering

4.96 out of 5 average rating, 228 reviews

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion designed by architects Bramhall Blenkharn Leonard. It sits on the edge of 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, woodland & chickens. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom,pizza oven,parking, walkable pub.

Feb 22 – Mar 1

R3,967 ZAR per night

Cottage in North Yorkshire

4.97 out of 5 average rating, 107 reviews

Katiann's Cottage

Accommodation Master Bedroom, en-suite shower 1 x King Size Bed, Freeview TV Twin Bedroom - 2 single beds TV Travel cot & highchair Bedlinen & Towels Bathroom - bath, shower, sink, toilet Kitchen Diner - dishwasher, washing machine, electric oven & hob, fridge, microwave, cooking utensils & iron Cosy lounge 2 sofas, Smart TV, electric log burner Gas Central Heating - Fuel & Electric Included Free Wi-fi 1 car parking public chargers nearby 1 x small dog subject to fee NO Smoking

Dec 18 – 25

R3,288 ZAR per night

Cottage in North Yorkshire

4.89 out of 5 average rating, 109 reviews

Luxury Cottage in the Heart of Pickering-Pets free

A beautifully appointed Cottage which is a true hidden gem! Nestled in the heart of the vibrant North Yorkshire market town of Pickering, on the very edge of the North Yorkshire Moors National Park. This luxury cottage boasts three roomy bedrooms set across 2 floors, sleeping up to 6 guests. With the recent addition of a luxury bathroom along with a cosy log burner, quaint courtyard and useful bike store. Child friendly with on street parking. We welcome dogs ( 2 for FREE).

Feb 3 – 10

R2,567 ZAR per night

Tiny home in Newton-on-Rawcliffe

4.99 out of 5 average rating, 187 reviews

The Hide NYM National Park Cosy Cabin with hot tub

Relaxing break for adults on the edge of the North York Moors. A 5 minute drive from Pickering, where you will find shops, bars and restaurants. York/Whitby 45 minute drive. Dalby Forest 30mins, Scarborough 40mins. A tranquil stay in a rural location. Ideal for walkers and cyclists. Includes hot tub. Contact me for discount if you would prefer not to use the hot tub Due to a balcony and limited space, The Hide is not suitable for babies, infants or children. Sorry, no pets.

Oct 22 – 29

R2,485 ZAR per night

Home in Kirkbymoorside

4.9 out of 5 average rating, 295 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.

Feb 4 – 11

R2,198 ZAR per night

Barn in North Yorkshire

4.92 out of 5 average rating, 143 reviews

Delightful Barn with log burner near Pickering

A tranquil, 19th century converted barn with private garden and outdoor fire overlooking the local countryside. A short drive from Pickering and close to the Moors, Whitby and York, the barn is great for a relaxing break. Inside, you will find a renovated living area, with a wood burning stove, Smart TV and fully fitted kitchen complete with oven, fridge washing machine and dish washer, the barn offers everything you will need for a relaxing getaway in Yorkshire.

Oct 9 – 16

R2,581 ZAR per night

Cottage in North Yorkshire

4.93 out of 5 average rating, 325 reviews

Castlegate Cottage

Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.

Jan 22 – 29

R2,941 ZAR per night

Cottage in North Yorkshire

4.91 out of 5 average rating, 200 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, Scarborough, Whitby and the historic walled city of York. Located on one of the main roads in Pickering, the tree lined street of Eastgate is beautiful in all seasons and the town centre is just a short walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Oct 4 – 11

R3,056 ZAR per night

Condo in North Yorkshire

4.94 out of 5 average rating, 127 reviews

🤍LUXURY apartment in the heart of Malton🤍#Chiltern

Enjoy a luxurious nights stay at this stylish apartment located in the heart of Malton, Yorkshire's food capital. Just a short walk away from all of the town's renowned amenities. Perfect for couple getaways or for the overnight business stopover. High-end furnishing, quaint balcony perfect for an evening drink in the summer, along with amenities steps from away from your doorstep. Alongside great public transport links to York, Leeds & Scarborough.

Sep 30 – Oct 7

R2,678 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Pickering vacation rentals

Free parking on premises

Air conditioning

Stay near Pickering's top sights

North Yorkshire Moors Historical Railway Trust Ltd69 locals recommend

Lidl4 locals recommend

The Black Swan Coaching Inn Pickering - Hotel & Restaurant3 locals recommend

Spice 4 U12 locals recommend

The White Swan Inn8 locals recommend

Beck Isle Museum15 locals recommend

Other great vacation rentals in Pickering

Home in North Yorkshire

5.0 out of 5 average rating, 22 reviews

The Bothy

Oct 2 – 9

R2,674 ZAR per night

Condo in North Yorkshire

4.95 out of 5 average rating, 92 reviews

Stylish 2 bedroom apartment with parking

Nov 4 – 11

R2,489 ZAR per night

Cottage in North Yorkshire

4.98 out of 5 average rating, 83 reviews

Lovely cottage for N. York Moors & Steam Trains

Feb 16 – 23

R2,404 ZAR per night

Cottage in North Yorkshire

4.94 out of 5 average rating, 63 reviews

Wren Cottage - 2 bedroom cosy cottage Pickering

Apr 26 – May 3

R2,829 ZAR per night

Cottage in North Yorkshire

4.9 out of 5 average rating, 52 reviews

Quaint Character Cottage Sleeps 4

Jun 18 – 25

R2,757 ZAR per night

Cottage in Pickering

4.98 out of 5 average rating, 96 reviews

Mill Cottage Is A Beautiful Cosy Country Escape

Sep 12 – 19

R3,659 ZAR per night

Home in North Yorkshire

4.94 out of 5 average rating, 17 reviews

Stationmaster's Cottage

Jun 20 – 27

R3,654 ZAR per night

Cottage in North Yorkshire

4.98 out of 5 average rating, 44 reviews

Quaint Yorkshire cottage with private parking

Feb 21 – 28

R3,115 ZAR per night

Quick stats about vacation rentals in Pickering

Total rentals
130 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
3.6K reviews
Nightly prices starting at
R950 ZAR before taxes and fees

Frequently Asked Questions

How much does it cost to stay in cottage rentals in Pickering?
Experience the best of Pickering with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Pickering?
Yes! Work meets play with ease at over 10 house rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Pickering have wifi?
Absolutely! We offer over 50 cottage rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Pickering?
Four-legged friends are welcome in Pickering. Choose from more than 20 house rentals for guests traveling with pets.
Do house rentals in Pickering have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Pickering have free parking?
Absolutely! We offer over 40 cottage rentals with free parking in Pickering. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Pickering?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 20 homes with free parking, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly house rentals in Pickering?
Pickering has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore