Cottage vacation rentals in Helmsley

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Top-rated cottage rentals in Helmsley

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Guest favourite

Cottage in Cawton

4.96 out of 5 average rating, 120 reviews

The Cake House

The Cake House is a cosy 3 bedroom country cottage situated in the picturesque village of Cawton, North Yorkshire. Perfect holiday location for stunning, rural walks, situated just a stones throw from The Ebor Way. Enjoy pub lunches and beautiful places to explore. York city Center- is a 30 min drive. Historic, market town Helmsley is 7 miles away, full of cosy coffee shops/ pubs/ restaurants and shops. Villages Hovingham and Gilling East (2-3 mile walk) both have great pubs and playgrounds.

Mar. 13 – 20

$292 CAD per night

Guest favourite

Cottage in East End

4.99 out of 5 average rating, 241 reviews

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

Jan. 24 – 31

$259 CAD per night

Guest favourite

Cottage in North Yorkshire

4.91 out of 5 average rating, 252 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/

Dec. 8 – 15

$140 CAD per night

Guest favourite

Cottage in Sessay

4.95 out of 5 average rating, 222 reviews

The Cobbler's Cottage

Nestled in the scenic North Yorkshire village of Sessay, this charming former cobbler's cottage offers a spacious retreat. Inside, you'll find a wood-burning stove, TV, Blu-ray player, and a modern kitchen equipped with an oven, microwave, dishwasher, fridge freezer, Nespresso coffee maker, and a washing machine. Step outside to a private patio complete with a dining area and barbecue. Plus, we warmly welcome one well-behaved pet, so you can bring your furry friend along if you desire.

Sep. 29 – Oct. 6

$166 CAD per night

Guest favourite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Braecote is a peaceful, warm, and welcoming cottage in the picture perfect village of Coxwold. With wide grass verges, honey coloured stone houses and a traditional country pub just up the road, Coxwold is one of the prettiest villages in North Yorkshire. York, Harrogate, Helmsley and Malton are close by, the North York Moors, Yorkshire Dales and east coast all within easy reach. Newburgh Priory is just up the road and Michelin starred Black Swan at Oldstead a short drive away.

Jan. 13 – 20

$173 CAD per night

Guest favourite

Cottage in Osmotherley

4.89 out of 5 average rating, 141 reviews

Cosy cottage in heart of North Yorks national park

Situated in one of the prettiest villages in the North York Moors National Park, this comfortable, cosy 250-year old cottage has open beams & a wood-burner, Wifi & SmartTV, and is beautifully furnished with good amenities and comfy beds. The village is a hub for walkers, cyclists and people wishing to enjoy the delights of the North Yorkshire hills which are on the doorstep. 3 great pubs & a well-stocked village shop nearby add to the enjoyment of staying in this lovely village.

Jun. 6 – 13

$178 CAD per night

Guest favourite

Cottage in North Yorkshire

4.99 out of 5 average rating, 189 reviews

The Barn at Cocker House in the heart of the Dales

Welcome to The Barn! Our charming 1-bedroom Cottage in Arkengarthdale offers breathtaking countryside views, perfect for couples or outdoor enthusiasts exploring the Yorkshire Dales. Immerse yourself in the beauty of rolling hills, lush fields, and meandering rivers. Take leisurely strolls or challenge yourself with hikes. The Barn provides a tranquil retreat with cozy ambiance and well-equipped amenities. Create lasting memories in this idyllic corner of Arkengarthdale.

Oct. 24 – 31

$204 CAD 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.

Mar. 19 – 26

$209 CAD per night

Guest favourite

Cottage in Helmsley

4.91 out of 5 average rating, 134 reviews

Cliff Stud Retreat, Helmsley, Frankel Cottage

Our 3 bedroom cottage has stunning countryside views due to its location. With a wood burner and cosy decor it's the perfect bolt hole for couple and families alike. Frankel cottage sleeps up to 5 guests (it’s advised 4 adults maximum) and has a fully equipped kitchen inc wm/microwave. The bathroom fully refurbished (shower/bath)is located downstairs. The cottage is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

Aug. 31 – Sep. 7

$358 CAD per night

Guest favourite

Cottage in North Yorkshire

4.96 out of 5 average rating, 302 reviews

Cosy barn*Castle Howard*Yorkshire Countryside*Coas

Set in the countryside within easy reach for pretty towns, the coast, York and various attractions, you will find "The Byre". This self-contained, barn with traditional beams, underfloor heating, and special touches, offers a relaxing retreat after a long day exploring. Your stay is made that little extra special...you can put your feet up with a Nespresso coffee, a boxset on Netflix or music on the Bose. Or now enjoy the sun with our new private garden.

Oct. 3 – 10

$193 CAD per night

Guest favourite

Cottage in North Yorkshire

4.91 out of 5 average rating, 202 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. 5 – 12

$223 CAD per night

Guest favourite

Cottage in Bewerley

5.0 out of 5 average rating, 280 reviews

The End Place - A romantic hideaway for two

The End Place is a self-contained cottage adjoining Moorhouse Cottage B&B. Downstairs is open plan, comprising a fully equipped kitchen and a living area with wood burning stove. A glass wall ensures uninterrupted views across Nidderdale Area of Outstanding Natural Beauty, as well as starry-night skyscapes. Upstairs opens out into a magical, fairy-lit, vaulted bedroom with a king size brass bed adorned with crisp linen and includes en suite with shower.

Feb. 24 – Mar. 3

$147 CAD per night