
Cottage holiday rentals in Helmsley
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Top-rated cottage rentals in Helmsley
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Stylish cottage for 2 in Bronte Country Haworth
Relax in style at this beautiful cottage in Haworth. A 2 min stroll leads to the home of the Bronte’s & the famous cobbled Main Street. Full of charm & character with original features such as beams; fireplaces; window seats & exposed Yorkshire stonework. Balances modern convenience with the uniqueness of a cosy cottage. An indulgent get away; statement bathroom; king bed; 1000 TC bedding; leather settees; bar stools & table; log burner; quality kitchen; Belfast sink. Renovated with love & care

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.

Seamstress Cottage Ripponden
Come and discover all Yorkshire has to offer in this beautifully renovated cottage with magnificent views over the countryside made famous by ‘Gentleman Jack’ and 'Happy Valley'. This stunning stone built mid-terraced over dwelling cottage can be found a short walk from the desirable West Yorkshire village of Ripponden and is full of traditional character and charm. Situated just 15 mins drive from The Piece Hall, Halifax and only 20 mins drive from popular visitor destination, Hebden Bridge.

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.

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.

Cliff Stud Retreat, Helmsley - Cecil Cottage
Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set on a horse stud farm surrounded by 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.

Luxury Old Stone Cottage, Beautifully Presented
Adults Only. No pets. The Old Chauffeurs Cottage, beautiful, luxurious, warm and cosy. Discounts for stays of 5 nights or more, please ask. 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.

Cosy barn in North Yorkshire near York & Coast
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.

Moxby Priory Cottage - An idyllic rural escape
Situated in picturesque farmland Moxby Priory Cottage offers a perfect base to explore everything that North Yorkshire has to offer. Just 10 miles from York this former granary dating back to 1840 has been lovingly renovated to offer a private retreat. The cottage is a delightful, spacious and fully equipped one bedroom property, with original high pitched ceiling, timber and stone flagged floors, lawned garden and private parking.

Seaves Mill luxury cottage Brandsby north of York.
Seaves Mill situated on the edge of The Howardian Hills in the North Yorkshire village of Brandsby 13.5 miles from the city of York. Seaves Mill has been converted into this beautiful living space by avid gardeners and architectural antique dealers Phil and Jo. The space has been designed with quality and decorative design in mind. It is set within beautifully landscaped gardens along side the picturesque Mill stream.
Popular amenities for cottage rentals in Helmsley
Cottage rentals with a hot tub

La Fenetre Holiday Cottage

Boutique Cottage with Hot Tub for 1 night stays

Morgan Cottage - Env Friendly - Private Hot Tub

Charming farm based cottage with hot tub/sauna

Rambling Rose Cottage, near Staithes

Preston Mill Loft, the relaxing retreat.

Luxury Farm Cottage with Hot Tub in Yorkshire

Langdale Cottage, located in North Yorkshire
Pet-friendly cottage rentals

Apple Tree Cottage. Stokesley.North Yorkshire.

Grooms Cottage by Sheriff Hutton Castle, Near York

Beulah House

Luxury cottage with views in beautiful Yorkshire

Charlie’s barn. A stunning barn conversion

2 Bed Barn in North York Moors National Park

Lovely cottage for N. York Moors & Steam Trains

Cottage on the Green next to historic castle
Private cottage rentals

Upside down stone Bothy on Marsden Moor

Cottage in the heart of Ryedale, North Yorkshire

Old Bald Peg, North York Moors, character cottage

Romantic Cottage with Hot Tub & Countryside Views

A grand getaway cottage in Masham, North Yorkshire

Idyllic and stylish private cottage by the stream

Foxglove Cottage

Fox Cottage in lovely Helmsley
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 $178 SGD per night before taxes and fees

Verified guest reviews
Over 830 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
10 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
- Robin Hood’s Bay
- yorkshire dales
- Flamingo Land Resort
- First Direct Arena
- Harewood House
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- York Castle Museum
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