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Holiday rentals in Pickering

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Top-rated holiday 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.

8–15 Nov

$161 SGD per night

Guest favourite

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.

15–22 Jun

$162 SGD per night

Guest favourite

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/

3–10 Mar

$139 SGD per night

Guest favourite

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.

22 Feb – 1 Mar

$284 SGD per night

Guest favourite

Cottage in North Yorkshire

4.97 out of 5 average rating, 108 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

18–25 Dec

$235 SGD 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).

3–10 Feb

$184 SGD per night

Guest favourite

Tiny home in Newton-on-Rawcliffe

4.99 out of 5 average rating, 188 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.

22–29 Oct

$178 SGD per night

Guest favourite

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.

4–11 Feb

$157 SGD per night

Guest favourite

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.

9–16 Oct

$185 SGD per night

Guest favourite

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.

22–29 Jan

$210 SGD per night

Guest favourite

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.

4–11 Oct

$219 SGD per night

Guest favourite

Apartment 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.

30 Sep – 7 Oct

$192 SGD per night

Holiday rentals for every style

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Houses

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Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Pickering holiday 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 holiday rentals in Pickering

Guest favourite

Home in North Yorkshire

5.0 out of 5 average rating, 22 reviews

The Bothy

2–9 Oct

$191 SGD per night

Guest favourite

Apartment in North Yorkshire

4.95 out of 5 average rating, 92 reviews

Stylish 2 bedroom apartment with parking

4–11 Nov

$178 SGD per night

Guest favourite

Cottage in North Yorkshire

4.98 out of 5 average rating, 84 reviews

Lovely cottage for N. York Moors & Steam Trains

16–23 Feb

$172 SGD per night

Guest favourite

Cottage in North Yorkshire

4.94 out of 5 average rating, 63 reviews

Wren Cottage - 2 bedroom cosy cottage Pickering

26 Apr – 3 May

$202 SGD per night

Guest favourite

Cottage in North Yorkshire

4.9 out of 5 average rating, 52 reviews

Quaint Character Cottage Sleeps 4

18–25 Jun

$197 SGD per night

Guest favourite

Cottage in Pickering

4.98 out of 5 average rating, 96 reviews

Mill Cottage Is A Beautiful Cosy Country Escape

12–19 Sep

$262 SGD per night

Guest favourite

Home in North Yorkshire

4.94 out of 5 average rating, 17 reviews

Stationmaster's Cottage

20–27 Jun

$262 SGD per night

Guest favourite

Cottage in North Yorkshire

4.98 out of 5 average rating, 44 reviews

Quaint Yorkshire cottage with private parking

21–28 Feb

$223 SGD per night

Quick stats about holiday 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
$68 SGD before taxes and fees

Destinations to explore