Cottage holiday rentals in Helmsley

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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!

Top-rated cottage rentals in Helmsley

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Top guest favourite
The lounge features a cozy setting with two leather settees facing a warm log burner, surrounded by rustic stonework. A TV is mounted on the wall, and a stylish table with high stools adds functionality. Natural light filters through shutted windows, illuminating the wooden floor.
Cottage in Haworth
4.99 out of 5 average rating, 341 reviews

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

Top guest favourite
The open-plan lounge displays exposed wooden beams overhead, featuring a large corner sofa in muted grey tones. A colorful armchair adds a pop of interest, while a feature fireplace with logs stacked alongside serves as a focal point. A Smart TV is positioned nearby, enhancing the cozy space.
Cottage in Grewelthorpe
4.95 out of 5 average rating, 369 reviews

Village Pub & Dogs, Spacious 4 Bed Cottage for 7

•🐾 Dog Friendly •🪵 Log Burner (first basket of logs included!) •🍽️ Large family dining table •🌳 Walks from the door - Hackfall Woods, Himalayan Gardens •🍻 Village pub 1- minute walk •🚗 Free parking (roadside) •🛌 4 Bedrooms - Ideal for 1-2 families or friends Escape to the peaceful village of Grewelthorpe in this warm dog friendly cottage just steps from a classic Yorkshire pub. Perfect for families or groups of up to 7 our cosy retreat features unforgettable walks straight from the door.

Guest favourite
Cottage in North Yorkshire
4.83 out of 5 average rating, 319 reviews

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.

Top guest favourite
The exterior of Manor House Cottage is framed by lush greenery and colorful flower beds. A well-kept lawn stretches in front, leading to the brick facade of the cottage, which features multiple windows and a welcoming entrance surrounded by trees.
Cottage in Thirsk
4.99 out of 5 average rating, 143 reviews

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.

Top guest favourite
The exterior of the cottage showcases a charming stone facade with a red-tiled roof. A staircase leads to the entrance, and a large parasol shades a wooden table and chairs on a gravel patio. Lush greenery and trees surround the property.
Cottage in East End
4.98 out of 5 average rating, 333 reviews

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!

Top guest favourite
A scenic view of a cottage by the River Seven is presented, with a backdrop of lush greenery and blooming daffodils adorning the riverbank. The charming stone building features a red-tiled roof and multiple windows reflecting the serene countryside.
Cottage in Sinnington
4.98 out of 5 average rating, 142 reviews

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.

Superhost
A cozy living room features a light wooden floor and a plush red area rug. A comfortable sofa is complemented by an armchair, with a coffee table positioned centrally. Artwork adorns the walls, and a modern fireplace sits at one corner. Natural light brightens the space.
Cottage in Helmsley
4.86 out of 5 average rating, 147 reviews

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.

Top guest favourite
Cottage in North Yorkshire
4.88 out of 5 average rating, 153 reviews

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.

Top guest favourite
Cottage in North Yorkshire
4.95 out of 5 average rating, 409 reviews

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.

Top guest favourite
A charming stone pathway leads to a rustic brick cottage, surrounded by well-tended gardens featuring a variety of plants and flowers. Two wooden garage doors are visible beside the cottage, while a wrought iron railing adds a classic touch to the outdoor space.
Cottage in Stillington
4.93 out of 5 average rating, 120 reviews

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.

Top guest favourite
The stone exterior of the cottage features a welcoming wooden door painted in soft green, adorned with a circular wreath. Above, a sign with the cottage's name hangs. Flower baskets with vibrant blooms enhance the entrance, complementing the rustic charm of the façade.
Cottage in Wrelton
4.98 out of 5 average rating, 421 reviews

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.

Top guest favourite
A cozy living room features a plush brown sofa and a plaid armchair, providing a comfortable seating area. A wooden coffee table sits in the center, and a flat-screen TV is positioned next to a rustic wooden entertainment unit. A modern fireplace adds warmth to the space.
Cottage in Seaton
4.98 out of 5 average rating, 172 reviews

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

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  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Helmsley
  6. Cottage rentals