
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 $236 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Helmsley holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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.

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.
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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.
LocationFamilyAccuracy

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!
ValueFamilyParks

Spacious character historic cottage
Our 17th Century, characterful Yorkshire longhouse provides a spacious, retreat, and a fantastic base for family and friends to meet up with plenty of opportunities for days out in the surrounding North York Moors. The house is in the vibrant market town of Pickering with it's famous heritage railway. Pickering has a cafes, restaurants and pubs along it's bustling high street and a weekly market selling fresh, local produce. 7+2 guests (sofa bed in the snug for 2 guests at an extra charge)
LocationFamilyComfort

Lovely cottage for N. York Moors & Steam Trains
19 Burgate is in the popular market town of Pickering, minutes’ walk from shops, eating places, Castle & Steam Railway (seasonal) - ideal for exploring the Moors, coastline & historic sights. It offers contemporary comfort, with a cosy living room, modern kitchen-diner, luxurious bathroom (walk-in shower, bath) & quality bedrooms. The garden offers eating/drinks outside and access to private parking. Prices are for 2 guests, with a small extra charge for the 2nd bedroom and well-behaved pets.
LocationFamilyCleanliness

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.
ValueFamilyCleanliness

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. Described by guests as "more of an experience than just a stay."
FamilyValueTV

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.
ValueFamilyNearby

Castlegate Cottage
Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.
ValueFamilyCleanliness

Rievaulx is a delightful one-bedroom cottage with kitchen and lounge.
Rievaulx is a delightful one-bedroom cottage with your own kitchen, lounge, and bathroom. We stand proudly in beautiful Bilsdale, six miles north of Helmsley, in the stunning North Yorkshire Moors National Park. It is surrounded by hills and open countryside which fringe the unique open moors. Traditionally built of Yorkshire stone in the seventies Laskill has its own private spring water supply that runs down from the hillside - definitely worth a sample.
FamilyLocationAccuracy

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.
ValueLocationBiking

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

Luxury Country Cottage Hot Tub Spa Retreat | York
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Charming farm based cottage with hot tub/sauna
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Historic 18th Hussars Cottage with a Modern twist
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3 Railway Cottage Pickering, Hot-Tub, Pets.
FamilyValueHot tub

Luxury Cottage close to Castle Howard with hot tub
ValueFamilyBathroom

Historic cottage, wood-fired hot tub + village pub
FamilyLocationWalkability

Luxury Farm Cottage with Hot Tub in Yorkshire
LocationFamilyAir conditioning

La Fenetre Holiday Cottage
ValueLocationTV
Pet-friendly cottage rentals

Fuchsia Cottage- a cosy getaway
LocationFamilyKitchen

2 bed Cottage Pickering, Priv Parking, Logburner
ValueFamilyGetting around

English country cottage on village green
FamilyLocationCheck-in

Cheerful & Quaint 18th Century cottage
LocationFamilyCleanliness

Winnow Cottage . in the Heart of the NY Moors
FamilyValueOutdoor spaces

Apple Tree Cottage. Stokesley.North Yorkshire.
FamilyLocationPets

Cosy character cottage in heart of Pickering
LocationFamilyCleanliness

Cosy ‘Cobblers Cottage’ - Pickering
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Private cottage rentals

Rowans Cottage - distinctive 1 bed restoration
FamilyLocationLayout

Moxby Priory Cottage - An idyllic rural escape
FamilyValueHospitality

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE
FamilyValueBiking

Florence Terrace
ValueFamilyWi-Fi

Farm Cottage with Stunning Views.
FamilyValueOutdoor spaces

Boundary Cottage, Spacious, Comfortable Cottage
FamilyValueBathroom

Matchbox Cottage Grade II listed building -Ripon
FamilyValueQuiet

Country cottage in the Yorkshire Dales
ValueLocationWalkability
Destinations to explore
- Yorkshire Dales National Park
- Yorkshire Coast
- Filey Beach
- Flamingo Land Resort
- Durham Cathedral
- Fountains Abbey
- Harewood House
- Bempton Cliffs
- York Castle Museum
- Bramham Park
- Scarborough Open Air Theatre
- York University
- Temple Newsam Park
- The Piece Hall
- York Minster
- Yorkshire Sculpture Park
- National Railway Museum
- Scarborough Beach
- Teesside University
- The Deep
- Peasholm Park
- Bridlington Spa
- Durham University
- First Direct Arena





