
Cottage holiday rentals in Helmsley
Find and book unique cottages on Airbnb
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 £126 per night before taxes and fees

Verified guest reviews
Over 890 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

4.7 Average rating
Helmsley stays receive an average rating of 4.7 out of 5 from guests
Top-rated cottage rentals in Helmsley
Guests agree: these cottages are highly rated for location, cleanliness and more.

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.

Old Fire Station Cottage | EV Charger | Opt 2nd BR
Contemporary Comfort in a Charming Cottage – Carlton-in-Cleveland, North York Moors National Park. Perfect for a quiet escape or an active adventure, this beautiful cottage offers everything you need Fast, reliable Wi-Fi & Smart TV Welcome goodies: fresh milk, coffee, sugar, tea, and delicious homemade cake Just a short stroll away, enjoy authentic Thai cuisine and top-notch real ales at the friendly village pub, The Blackwell Ox – also offering excellent takeaway options. EV Charger by App

Luxury hideaway cottage nestled in Yorkshire Dales
A luxury stone cottage nestled in the Yorkshire Dales, a short stroll from the local pub and 1.4 miles away from the market town of Masham, Hideaway is the perfect place to cosy up in front of the wood burning stove or explore the beautiful countryside with walks from the door. The stylish interior combines contemporary design with quirky original features to create a romantic retreat you'll want to revisit. Pets welcome, high speed wifi, off street parking, garden & summerhouse workspace.

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.

Pretty Yorkshire Stone Cottage Harome
A charming stone cottage situated in the picturesque village of Harome, 3 miles from the market town of Helmsley.This characterful cottage is up to date with everything you need without losing original features of beamed ceilings & a cosy log burner. The cottage offers luxe accommodation with a spacious kitchen, two delightful bedrooms, a power shower, bath, well equipped kitchen & hotel grade linen. A cosy sitting room with open plan dining area. There is a little garden outside with a table.

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/

Foxglove Cottage
Foxglove, a gorgeous little one bed cottage, with its' own kitchen, bathroom, lounge and outdoor seating area. Perfect for an intimate getaway. Standing proudly in beautiful Bilsdale, six miles north of Helmsley, in the stunning North Yorkshire Moors National Park. We are surrounded by hills and open countryside which fringe the unique open moors. It is also part of a collection of other 8 properties (previously a working farm) that can be booked individually or exclusively all together.

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.

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.

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.
Popular amenities for cottage rentals in Helmsley
Cottage rentals with a hot tub

Sundial Cottage, Stunning 3Bed Cottage with Hottub

Morgan Cottage - Env Friendly - Private Hot Tub

Charming farm based cottage with hot tub/sauna

Historic cottage, wood-fired hot tub + village pub

Preston Mill Loft, the relaxing retreat.

Historic 18th Hussars Cottage with a Modern twist

Harwood Cottage, A Cosy 1 Bed Cottage

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

Cosy 1-bedroom cottage with indoor log burner

Castlegate Cottage

St Anthony’s, bright perkily decorated 3 b/r house

Fuchsia Cottage- a cosy getaway

Lovely cottage for N. York Moors & Steam Trains

Fully Fenced Dog Field, Sea Views & Forest Walks

Cosy Country Cottage Sleeps 4

Luxury Yorkshire cottage with stunning rural views
Private cottage rentals

Stylish cottage for 2 in Bronte Country Haworth

Seamstress Cottage | Panoramic valley views

Imagine at High Parks

Farndale Cottage North York Moors National Park

Idyllic and stylish private cottage by the stream

Cosy barn in North Yorkshire near York & Coast

Cottage with beautiful views

Characterful one bed property above Hebden Bridge
Destinations to explore
- House rentals Helmsley
- Rentals with a patio Helmsley
- Pet-friendly rentals Helmsley
- Rentals with a fireplace Helmsley
- Family-friendly rentals Helmsley
- Rentals with a washing machine and dryer Helmsley
- Cabin rentals Helmsley
- Cottage rentals North Yorkshire
- Cottage rentals England
- Cottage rentals United Kingdom
- Yorkshire Dales National Park
- yorkshire dales
- Yorkshire Coast
- Flamingo Land Resort
- Filey Beach
- Durham Cathedral
- Bempton Cliffs
- Harewood House
- Fountains Abbey
- York Castle Museum
- Bramham Park
- Scarborough Open Air Theatre
- National Railway Museum
- Temple Newsam Park
- Royal Armouries Museum
- York University
- The Piece Hall
- University of Leeds
- Durham University
- York Minster
- Scarborough Beach
- Teesside University
- Yorkshire Sculpture Park
- The Deep





