
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.

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 Smithy at Cross Pipes, Goathland
The Smithy is a self contained stone built cottage situated on the edge of the beautiful North Yorkshire Moors. It was built in the 1800’s and was originally one of two blacksmiths serving the community of Goathland. The Smithy offers you a comfortable base to visit the local area. Spacious studio accommodation with a king sized bed in a recessed area, walk in shower and toilet, full kitchen facilities, wood burning stove, TV and Wi-Fi. There is an outside seating area and private parking.

Cosy one bedroom cottage in Pickering
This lovely cottage is nestled in the centre of the beautiful market town of Pickering, Relax at this charming cottage which offers easy access to the enchanting landscapes of the North Yorkshire Moors and the nearby towns and coast. Whether you visit the iconic North Yorkshire Moors Railway, attend a concert at the Scarborough Open Air Theatre, or spend a day at the beach or exploring Whitby and the Moors. If you are seeking relaxation or adventure, this unique getaway is the perfect choice.

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE
Detached holiday cottage Sleeps two (ONE DOUBLE BED) FREE WIFI Off road parking En-suite bathroom Fully equipped kitchen TV and fridge freezer Microwave Ideal location for all local attractions 2 minute walk into Pickering and local pubs, restaurants and shops Quotes from past guests: it's just perfect/best cottage we've stayed in/everything is so welcoming/ location is fantastic Places to visit in North Yorkshire http://www.iknow-yorkshire.co.uk/attractions/north_yorkshire/

Winnow Cottage . in the Heart of the NY Moors
Winnow Cottage is set in the idyllic North York Moors National Park. Dating back to the 1800s, the cottage has an open plan living and dining area with a kitchen and two en-suite double bedrooms. Patio doors lead out to a private decked area with views of the moors. The cottage is dog-friendly, 2 dogs welcome and accessed via a 1/4 mile rough single bridle track. There are many walking and cycling routes from the cottage and it is well-situated for exploring beautiful North Yorkshire.

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.

Luxury Cottage close to Castle Howard with hot tub
Bumble Bee Cottage, a luxury 2 bedroomed holiday home featuring a private hot tub (on request) with a large private garden. Relax & unwind in this peaceful property, set back from the road in the pretty village of Welburn in the heart of The Howardian Hills. Castle Howard is approximately 1 mile away & is walkable from Bumble Bee. Welburn has a pub/restaurant & a shop/bakery. Yorkshires Food Capital, Malton is a 5 mile drive away & the beautiful city of York only 15 🐝

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.

Country cottage five miles from the City of York
Naburn Grange Cottage is a farm worker’s cottage attached to an 18th century riverside farmhouse in between the villages of Naburn and Stillingfleet. With easy access to York by car, bus, cycle track or (in the summer months) riverbus, you can explore the city’s history or the beauty of the surrounding countryside. This one-bedroomed cottage is well-equipped and private, with the owners next door for information or advice on your visit.
Popular amenities for Helmsley cottage rentals
Cottage rentals with free parking

2 bed Cottage Pickering, Priv Parking, Logburner

17th Century fisherman's cottage + stunning view

Stonebeck Cottage - The Perfect Country Hideaway

Idyllic and stylish private cottage by the stream

Titus - A hidden gem with stunning views

Cosy 2 Bed Seaside Cottage, Robin Hoods Bay Whitby

Historic cottage, wood-fired hot tub + village pub

Historic 18th Hussars Cottage with a Modern twist
Cottage rentals with a hot tub

La Fenetre Holiday Cottage

Laburnum Cottage, Middlestone.

Jenson Cottage - Env Friendly & Private Hot Tub

Charming farm based cottage with hot tub/sauna

Preston Mill Loft, the relaxing retreat.

Langdale Cottage, located in North Yorkshire

Rose Cottage -hot tub, dog friendly, country views

Larch Cottage Ruston with hot tub, dogs go free
Pet-friendly cottage rentals

Luxury By The Brook

The Old Coach House, in Harrogate, Sleeps 4

Charlie’s barn. A stunning barn conversion

Plum Tree Cottage - 1 bedroom

Saltburn l The Outlook- Sea views, Dog friendly.

Character cottage in idyllic rural village

Cosy Country Cottage Sleeps 4

Cheerful & Quaint 18th Century cottage
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 ﺩ.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 810 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Helmsley vacation 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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