
Cottage holiday rentals in Helmsley
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Top-rated cottage rentals in Helmsley
Guests agree: these cottages are highly rated for location, cleanliness and more.

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

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, steam railway, the coast 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.

Historic cottage, log-burning tub & village pub
Unwind in this beautifully restored Grade II listed, 17th Century farmers cottage with exposed beams, original ironwork, underfloor heating and a soothing log burning hot tub. Opposite you'll find a cosy, dog-friendly village pub with open fires. You’ll be 7 minutes away from artisanal food producers in the market town of Malton (known as Yorkshire's Food Capital) and ideally located for exploring the Yorkshire Wolds (2 miles), Howardian Hills (10 miles), York (17 miles) & Beaches (27 miles).

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!

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.

Goose End Cottage, North Yorkshire
Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

Whootin Owl Barn
Whootin Owl Barn is a smart luxury detached barn with private screened hot tub and gravelled fire pit area overlooking private woodland on a tranquil country lane in the heart of North Yorkshire only 9 miles from Castle Howard and 30 mins from York City Centre. 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 North Yorkshire
Tarrs Yard is a beautifully restored early 18th century cottage, nestled in the valley between York and Malton. Ideal for walkers and nature lovers, the cottage is just a short drive from Castle Howard and close to the North Yorkshire Moors, Dalby Forest and the Yorkshire Coast. In a picturesque setting surrounded by uninterrupted views of the Howardian Hills and the Yorkshire Wolds, the cottage is perfectly positioned to enjoy the best of the great outdoors.

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

Cosy barn*York*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 in theprivate garden.

The End Place - A romantic hideaway for two
The End Place is a self-contained cottage adjoining Moorhouse Cottage. 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.

Beautiful 1-bed hideaway in rural North Yorkshire
Nestled in the heart of rural North Yorkshire - Skylark is the perfect hideaway to take some time out and unwind. Wake up to amazing views across our meadows up to The White Horse of Kilburn. One mile outside the bustling market town of Easingwold, half way between York and the North York Moors, Skylark makes the perfect base to explore the best Yorkshire has to offer. We're down some narrow country lanes, so make sure to bring a map!
Popular amenities for cottage rentals in Helmsley
Cottage rentals with a hot tub

Family/Dog friendly cottage & hot tub

Highbury Farm Cottage with Hot Tub. Pet friendly

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

Charming farm based cottage with hot tub/sauna

Preston Mill Loft, the relaxing retreat.

Historic 18th Hussars Cottage with a Modern twist

Rose Cottage -hot tub, dog friendly, country views

Luxury Cottage close to Castle Howard with hot tub
Pet-friendly cottage rentals

The Old Coach House, in Harrogate, Sleeps 4

17th Century fisherman's cottage + stunning view

Beulah House

Luxury cottage with views in beautiful Yorkshire

Stonebeck Cottage - The Perfect Country Hideaway

Saltburn l The Outlook- Sea views, Dog friendly.

Lovely cottage for N. York Moors & Steam Trains

The Shepherds Cottage, Stillington, York
Private cottage rentals

The Piggery Barn (Deluxe), in Nidderdale AONB

Luxurious 2 bed barn in Michelin food zone

Old Bald Peg, North York Moors, character cottage

Foxglove Cottage

Cottage with beautiful views

Fox Cottage in lovely Helmsley

Country cottage in the Yorkshire Dales

Old Fire Station Cottage, EV point Opt. 2nd B’room
Quick stats about cottage rentals in Helmsley

Total holiday rentals
Explore 30 holiday rentals in Helmsley

Nightly prices starting at
Helmsley holiday rentals start at € 113 per night before taxes and fees

Verified guest reviews
Over 790 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Helmsley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Helmsley rentals

4.8 Average rating
Helmsley stays are highly rated by guests – averaging 4.8 out of 5!
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- Yorkshire Dales national park
- Flamingo Land Resort
- yorkshire dales
- Fountains Abbey
- Harewood House
- Durham Cathedral
- National Railway Museum
- Royal Armouries Museum
- York Castle Museum
- North Yorkshire Water Park
- Hartlepool Sea Front
- Cayton Bay
- Saltburn Beach
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