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Cottage vacation rentals in Helmsley

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Top-rated cottage rentals in Helmsley

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Cottage in Staithes

4.81 out of 5 average rating, 160 reviews

17th Century fisherman's cottage + stunning view

Wake up to this stunning view, relax, and enjoy your morning coffee, afternoon tea or early evening G&T sitting outside our traditional cottage gazing at the fishing boats in the beck, higgledy-piggledy rooftops or out to sea. Regularly stayed in and painted by artists, this charming 17th Century cruck-beamed fisherman's cottage is quaint and cosy + open fire-ideal for a romantic getaway or walking holiday. Mortimer & Whitehouse stayed and filmed their Gone Fishing Christmas Special here 2020.

Cottage in North Yorkshire

4.84 out of 5 average rating, 108 reviews

Luxury Old Stone Cottage, Beautifully Presented

We do not accept children or pets. The Old Chauffeurs Cottage, beautiful, luxurious, warm and cosy. Two bedrooms with comfortable King size beds and a great lounge and kitchen. A downstairs toilet & full bathroom upstairs. It provides a good base for walkers & sightseers as we are close to the North York Moors, the steam railway at Pickering, Castle Howard & York. There is free WiFi & parking plus secure storage for cycles. We have a short video Youtube@tara101 playlist The Chauffeurs Cottage

Cottage in North Yorkshire

4.96 out of 5 average rating, 220 reviews

Dryden Cottage, Whitby Harbour - Beach side

This cottage is all about the view! Beach-side location at the base of the 199 steps - perfect for exploring the beautiful historic town of Whitby. Browse in the eclectic independent shops and sample the finest seafood in the local eateries. Walk up to the abbey, stroll along the piers and collect fossils from the beach, take a ride on the steam train to the neighbouring villages and explore the moors. Please note due to the beach side location of the cottage, there is unfortunately no parking.

Cottage in Cawton

4.97 out of 5 average rating, 145 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.

Cottage in East End

4.99 out of 5 average rating, 269 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!

Cottage in North Yorkshire

4.99 out of 5 average rating, 110 reviews

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

Cottage in North Yorkshire

4.92 out of 5 average rating, 293 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/

Cottage in North Yorkshire

4.91 out of 5 average rating, 242 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 (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Cottage in Coxwold

4.99 out of 5 average rating, 173 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.

Cottage in Bewerley

5 out of 5 average rating, 311 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.

Cottage in York

5 out of 5 average rating, 405 reviews

Whootin Owl Barn

Whootin Owl Barn is a smart luxury detached barn with private screened hot tub overlooking private woodland on a tranquil country lane in the heart of North Yorkshire only 9 miles from Castle Howard and 25 mins from York. If you are looking for a romantic modern and ultra clean property in a beautiful private location for a short break or Holiday getaway or looking for a base to explore North Yorkshire, look no further.

Cottage in Wrelton

4.98 out of 5 average rating, 352 reviews

Old Forge in Wrelton, North Yorkshire.

This cottage, in the village of Wrelton near Pickering, was a 19th century blacksmith's forge and has now been renovated into a delightful living space complete with fully-equipped kitchen, large living room area, bathroom with walk-in shower and a cosy bedroom located on a mezzanine floor which is reached via a spiral staircase. The Old Forge offers a great location for a relaxing stay in beautiful North Yorkshire.

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Popular amenities for Helmsley cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Scotton

4.96 out of 5 average rating, 137 reviews

Family/Dog friendly cottage & hot tub

Cottage in Middlestone

4.96 out of 5 average rating, 194 reviews

Laburnum Cottage, Middlestone.

Cottage in Duggleby

4.91 out of 5 average rating, 273 reviews

Highbury Farm Cottage with Hot Tub. Pet friendly

Cottage in Newbridge

4.93 out of 5 average rating, 131 reviews

3 Railway Cottage Pickering , Hot Tub, Pets all'd

Cottage in Newton-on-Rawcliffe

4.98 out of 5 average rating, 129 reviews

Charming farm based cottage with hot tub/sauna

Cottage in Burythorpe

4.99 out of 5 average rating, 134 reviews

Salt water hot/cold tub + dog friendly nr. Malton

Cottage in Rosedale Abbey

4.9 out of 5 average rating, 107 reviews

Orchard House, luxury cottage retreat.

Cottage in Harwood Dale

4.92 out of 5 average rating, 123 reviews

Harwood Cottage, A Cosy 1 Bed Cottage

Pet-friendly cottage rentals

Cottage in Hebden

4.95 out of 5 average rating, 190 reviews

Luxury By The Brook

Cottage in Robin Hood's Bay

4.85 out of 5 average rating, 169 reviews

Hilda Cottage, bottom of Robin Hoods Bay!

Cottage in Stokesley

4.9 out of 5 average rating, 244 reviews

Apple Tree Cottage. Stokesley.North Yorkshire.

Cottage in Ampleforth College

4.93 out of 5 average rating, 215 reviews

St Anthony’s, bright perkily decorated 3 b/r house

Cottage in Easingwold

4.97 out of 5 average rating, 124 reviews

Beautiful 1-bed hideaway in rural North Yorkshire

Cottage in North Yorkshire

4.95 out of 5 average rating, 105 reviews

Lovely cottage for N. York Moors & Steam Trains

Cottage in Great Barugh

4.85 out of 5 average rating, 121 reviews

Charming renovated barn with wood burning stove

Cottage in East Riding of Yorkshire

4.97 out of 5 average rating, 362 reviews

The Hayloft at Bainton - 2 bedroom cottage.

Private cottage rentals

Cottage in Haworth

4.99 out of 5 average rating, 237 reviews

Stylish cottage for 2 in Bronte Country Haworth

Cottage in Osmotherley

4.88 out of 5 average rating, 162 reviews

Cosy cottage in heart of North Yorks national park

Cottage in Holtby

4.93 out of 5 average rating, 149 reviews

The Applebarn is a cosy little Holtby Home

Cottage in Ripon

4.99 out of 5 average rating, 212 reviews

Cottage with beautiful views

Cottage in Pickering

4.98 out of 5 average rating, 122 reviews

Mill Cottage Is A Beautiful Cosy Country Escape

Cottage in North Yorkshire

4.99 out of 5 average rating, 153 reviews

Two Bedroom Luxury Cosy Cottage With Parking

Cottage in West Yorkshire

4.97 out of 5 average rating, 259 reviews

Molly's Cottage

Cottage in Darley

4.99 out of 5 average rating, 297 reviews

Country cottage in the Yorkshire Dales

Quick stats about cottage rentals in Helmsley

Total rentals
20 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
440 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

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