
Cottage vacation 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.

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).

Manor House Cottage self catering rural location
Manor House Cottage is located in the small hamlet of Holme-On-Swale 7 miles from the market town of Thirsk which is known for its connection to James Herriott and within easy reach of North Yorkshires National Parks. Set within the grounds of the Manor House, It is a quirky upside down cottage with a well appointed modern kitchen, two bedrooms and bathroom on the ground floor with sitting room upstairs, private garden with table and chairs. There are no other holiday cottages in the grounds.

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.

Cliff Stud Retreat, Helmsley - Cecil Cottage
Cecil cottage is A three bedroom cosy cottage set within the 220 acres Cliff Stud retreat estate, with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen. The bathroom has a shower/bath & is fully refurbished and located downstairs. The cottage boasts it's own garden with fruit trees and is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

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.

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.

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.
Popular amenities for Helmsley cottage rentals
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.

New 2023 mini moon luxe with hot tub copper bath

Historic 18th Hussars Cottage with a Modern twist

Poppy Cottage No 1 with hot tub-2 miles to Skipton
Pet-friendly cottage rentals

Grooms Cottage by Sheriff Hutton Castle Near York

Cosy 1-bedroom cottage with indoor log burner

Unique 18thC Yorks Dales Silk Weavers’ mill house.

The Garden House in Low Catton

Kilburn Chicken Cottage

Lovely cottage for N. York Moors & Steam Trains

The Shepherds Cottage, Stillington, York

Picturesque Cottage in Stonegate, Lealholm
Private cottage rentals

The Piggery Barn (Deluxe), in Nidderdale AONB

17th Century fisherman's cottage + stunning view

Romantic Cottage with Hot Tub & Countryside Views

Dryden Cottage, Whitby Harbour - Beach side

Cottage with beautiful views

Fox Cottage in lovely Helmsley

Characterful one bed property above Hebden Bridge

Rowans Cottage - distinctive 1 bed restoration
Quick stats about cottage rentals in Helmsley
Total vacation rentals
Explore 30 vacation rentals in Helmsley
Nightly prices starting at
Helmsley vacation rentals start at $182 CAD per night before taxes and fees
Verified guest reviews
Over 790 verified reviews to help you choose
Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 of Helmsley vacation 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
- North Yorkshire Water Park
- York Castle Museum
- Hartlepool Sea Front
- Cayton Bay
- Studley Royal Park
- Saltburn Beach
- Scarborough South Cliff Golf Club
- Locomotion
- Ganton Golf Club
- Malham Cove
- Ryedale Vineyards
- Semer Water
- The Bowes Museum
- York Art Gallery
- Scarborough Beach
- Filey Beach