
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.

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

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.

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.

Upside down stone Bothy on Marsden Moor
Long Fall Bothy is a gorgeous stone building on the outskirts of Marsden village in West Yorkshire. Perfect for a walking holiday, the Kirklees Way passes the property and the Pennine Way, Oldham Way are close by. A great place for mountain biking with the Transpennine Trail a few miles away and lots of cycle paths/trails on your doorstep. Local real ale pubs and plenty of cafes in Marsden village a short walk (15 minutes) along the canal. Beautiful scenery, views from the cottage are amazing.

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!

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.

Farm Cottage with Stunning Views.
Nestled in the heart of the North Yorkshire Moors on our 100 acre Jacob Sheep Farm, close to the villages of Danby (3.9 miles) and (Castleton 3.7 miles) We are nothing like a hotel but instead offer quirky, comfortable, open plan, home from home accommodation in a tranquil setting. Arriving on foot, it is fully equipped with everything you might need. Close to Danby Castle wedding venue. We welcome all family pets and have plenty of fields for off lead exercise.

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.

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.

Oomwoc Cottage
Follow us on social media @oomwoccottage Welcome to Oomwoc Cottage, a charming cow-themed country cottage nestled in the serene village of Seaton, East Yorkshire. A unique and tranquil retreat, the perfect escape for those looking to experience the beauty of rural living with a delightful touch of whimsy Step inside and be greeted by a warm and inviting space, rustic elegance meets playful cow-inspired décor.
Popular amenities for cottage rentals in Helmsley
Cottage rentals with a hot tub

Sundial Cottage, Stunning 3Bed Cottage with Hottub

Jenson Cottage - Env Friendly & Private Hot Tub

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

Charming farm based cottage with hot tub/sauna

Preston Mill Loft, the relaxing retreat.

Luxury Farm Cottage with Hot Tub in Yorkshire

Langdale Cottage, located in North Yorkshire

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

2 bed Cottage Pickering, Priv Parking, Logburner

Apple Tree Cottage. Stokesley.North Yorkshire.

Grooms Cottage by Sheriff Hutton Castle, Near York

Beulah House

Charlie’s barn. A stunning barn conversion

Cozy Cottage by Shibden Hall, Halifax

Castlegate Cottage

Saltburn l The Outlook- Sea views, Dog friendly.
Private cottage rentals

Lovely, cosy cottage in the heart of Osmotherley

Cottage in the heart of Ryedale, North Yorkshire

Romantic Cottage with Hot Tub & Countryside Views

Idyllic and stylish private cottage by the stream

Imagine at High Parks

Titus - A hidden gem with stunning views

Cottage with beautiful views

Country cottage in the Yorkshire Dales
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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- Flamingo Land Resort
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- Fountains Abbey
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- Durham Cathedral
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