
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.

The Old Coach House, in Harrogate, Sleeps 4
Centrally-located cottage, walking distance to Harrogate town centre. Recently refurbished. 2 bedrooms, 1 king & 2 singles (2'6"). Shower room. Kitchen with dishwasher, large fridge/freezer and washer/dryer. Terraces, giving you morning, afternoon and evening sun (Weather permitting). Lovely view over the historical St Luke's Court Church. Array of restaurants and bars & shops in walking distance. 7mins walk to Harrogate's Convention Centre. Quiet on street parking with disk/permit provided.

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.

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.

Apple Tree Cottage. Stokesley.North Yorkshire.
A delightful old cottage overlooking West Green with a mix of antique, upcycled and vintage inspired decoration. The cottage is dog friendly, with a patio and large enclosed, secure garden. Located on the outskirts of the historic market town. The town has a distinguished wide cobbled high street lined with Georgian and Victorian buildings. It is served by banks,shops, up market restaurants and pubs. Surrounded by the Yorkshire Moors it makes an ideal base for exploring the Dales & East coast.

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!

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.

Luxury Old Stone Cottage, Beautifully Presented
Adults Only. No 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 Free WiFi & parking plus secure storage for cycles. We have a short video (copy & past) Youtube@tara101 playlist The Chauffeurs Cottage

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.

Historic cottage, wood-fired hot tub + village pub
Three hundred year old sandstone, exposed timber beams, and the kind of warmth that comes from old walls, open fires and underfloor heating. Yew Tree Cottage @ Kingfisher and Yew sits opposite a dog-friendly village pub. Take long walks from the front door. Light the wood-fired hot tub in the walled garden and toast your toes by the fire. This Grade II listed cottage is seven minutes from the market town of Malton. Featured in Living North's top self catering retreats.

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.

Cliff Stud Retreat, Helmsley - Cecil Cottage
Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set within the 220 acres 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, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.
Popular amenities for Helmsley cottage rentals
Cottage rentals with a hot tub

La Fenetre Holiday Cottage

Jenson Cottage - Env Friendly & Private Hot Tub

Charming farm based cottage with hot tub/sauna

Langdale Cottage, located in North Yorkshire

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

Holly Tree Cottage
Pet-friendly cottage rentals

2 bed Cottage Pickering, Priv Parking, Logburner

Stylish cottage near York, pool table 3 bed 3 bath

Kilburn Chicken Cottage

Lovely cottage for N. York Moors & Steam Trains

Fully Fenced Dog Field, Sea Views & Forest Walks

Romance or a rest at The Nest Castleton,Whitby!

The Shepherds Cottage, Stillington, York

Stylish and comfortable converted stable in Masham
Private cottage rentals

The Rabbit Hole cosy cottage near Bolton Abbey

Grooms Cottage by Sheriff Hutton Castle, Near York

Romantic Cottage with Hot Tub & Countryside Views

Cosy 2 Bed Seaside Cottage, Robin Hoods Bay Whitby

Saltburn l The Outlook- Sea views, Dog friendly.

Fox Cottage in lovely Helmsley

The Cow House, in the heart of old town Whitby.

The Hayloft - Luxury Bolthole
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 $156 AUD per night before taxes and fees

Verified guest reviews
Over 810 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Helmsley holiday rentals include Wi-Fi 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
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