
House vacation rentals in Helmsley
Find and book unique houses on Airbnb
Quick stats about house rentals in Helmsley

Total vacation rentals
Explore 10 vacation rentals in Helmsley

Nightly prices starting at
Helmsley vacation rentals start at ﺩ.ﺇ 808 per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

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

Wi-Fi availability
10 of Helmsley vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Helmsley rentals

4.9 Average rating
Helmsley stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Helmsley
Guests agree: these houses are highly rated for location, cleanliness, and more.

Central Fully Ensuite house sleeps 6 dog friendly
The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.
FamilyLocationWalkability

Highfield Annex with off St Parking in Keldholme
Enjoy a tranquil getaway at Heather Annex! Explore the North York Moors by foot; cycle Dalby Forest’s trails or ride the iconic Pickering steam train to Whitby. Visit charming market towns like Helmsley and Kirkbymoorside. Nearby, discover TV's 'Bangers & Cash' or York. Coastal towns, Whitby & Scarborough are less than an hour away. Walk to local pubs and cafes. Return to 1/2 an acre of grounds featuring American Miniature Horses & hens. Or simply unwind on the Patio & have a peaceful stay!
FamilyValueAccess

Country Cottage with Steam Railway Views.
Positioned on a pedestrian road, wake up to the sound of birds or the steam railway. Cosy up to the log burner or sit out in the evening sun, on our west facing decking overlooking the railway. 1 minute walk to forest paths and Pickering castle, or a 2 minute walk to the town centre; you couldn’t be more perfectly located. Pickering has the charm of a rural North Yorkshire town with all the amenities you need for a relaxing break or a family centred vacation. Discounts for stays over 2 nights.
ValueLocationQuiet

Stationmaster's Cottage
A detached Victorian stone cottage in the shadow of Pickering Castle and overlooking North York Moors Railway station, this characterful property with real fire is only 3 minutes walk away from town centre amenities, the castle and a ten minute walk to the start of the Tabular Hills way and gateway to the North York Moors National Park. Free parking is provided in the Platform 3 Car Park diagonally opposite the property 70 yards away (dashboard pass provided). Please note: steep stepped access.
LocationValueHeating

Country Manor House - Nr Richmond North Yorkshire
No.2 West Layton Manor is part of an Historic Victorian Manor House built in 1872. The property provides the perfect setting for families and friends gathering for special occasions or holidays in beautiful North Yorkshire. The property boasts 6 kingsize bedrooms equipped with 6 full ensuite bathrooms. A further 7th bathroom is located on the ground floor. There are 3 large reception rooms, 2 open log fires, and approximately 1/2 an acre of gardens. There is private parking for 8 vehicles.
ValueFamilyCheckout

Gorgeous country cottage, Nawton near Helmsley
A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.
ValueLocationQuiet

Little Hillside
A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to relax, listen to the wildlife and enjoy the beautiful countryside. The pretty market town Helmsley is less than 10 minutes drive, with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants. York is 45 mins drive and an hour to the coast for beach walks.
ValueFamilyHospitality

The Town House
This family and dog friendly three storey town house in the centre of Kirkbymoorside gives easy access to shops, pubs, the local market and childrens play area, and a 1 minute walk finds you in open fields with public footpaths. Stroll around the outskirts of town or head off on foot to explore the moors, woodlands and villages. The coast, Dalby and Cropton forest, North York Moors National Park, Pickering steam railway, Flamingoland, Malton and the city of York are in easy driving distance.
ValueFamilyHeating

Spacious two bedroom country property
Granary Lodge is situated on a quiet lane, yet less than two miles from Thirsk; a busy, attractive market town. It is spacious with a large lounge, kitchen, a double bedroom (ensuite bathroom) and a twin room. Also, a shower room with basin and toilet. Enjoy the use of your private patio seating area with views over the owners garden and pond. A larger garden area and further seating is also available for guest use. Local good pub (15 mins walk). N York Moors National Park: 15 mins drive.
FamilyValueParks

Oakforge Cottage, a spacious home from home.w
Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.
ValueLocationComfort

Home Cottage -North Yorkshire - Dog Friendly
Picture perfect Stone cottage located in the heart of the pretty village of Hovingham, on the edge of the Howardian Hills, an area of outstanding natural beauty. 2 bedrooms and 2 bathrooms. Cosy lounge with log burner and smart tv and of course wifi. A fully equipped Country style kitchen, with dining area and a Utility Room = the perfect dog bedroom!! Enclosed Courtyard garden. Perfect holiday retreat
LocationFamilyCleanliness

Beautiful, quiet and private historic Coach House
My place is in the heart of the North York Moors and close to the Yorkshire Heritage Coast. surrounded by stunning views, open countryside and within easy reach of all the attractions of the Yorkshire moors. The property is in an unspoilt, peaceful and idilic location. with private courtyard parking and established gardens
ValueLocationQuiet
Popular amenities for Helmsley house rentals
House rentals with a pool

Langton Hall - Grade 2 listed
FamilyValueCleanliness

Cosy 2 bedroom river/coastal retreat. Heated pool.
ValueLocationDecor

Salty Kisses, The Bay, Filey
FamilyLocationCleanliness

The Elliott Suite @ Southfield Barton-UponHumber
LocationFamilyGetting around

Brand new 2021 ABI WINDERMERE STATIC Cedar 1
ValueLocationParking

The Hideaway with Private Pool Sleeps 2
FamilyLocationNearby

West End Farm
FamilyHospitalityPets

Apple Cottage | One Bedroom, Indoor Pool & Gardens
FamilyLocationAmenities
Weekly house rentals

The Shed, Hovingham, York
FamilyLocationAmenities

Luxury house in an acre of gardens 15 mins to York
LocationValueParks

The Old Post Office pretty village 20min from York
FamilyLocationHospitality

Explore North Yorkshire. Large, stylish farmhouse
FamilyLocationDecor

Luxury 3 bedroom house - hot tub & amazing view!
LocationFamilyComfort

The Sanctuary, Pet friendly
ValueLocationQuiet

Short stroll to pubs, cafés & shops. Free Parking
ValueLocationDecor

Spacious house in central Harrogate with parking
LocationFamilyHeating
Private house rentals

Abbey Cottage, Rievaulx, Near Helmsley, Yorkshire
LocationFamilyView

The Mill House, spacious barn conversion
FamilyLocationOutdoor spaces

Wass, 3 bed, Cottage near Ampleforth
FamilyLocationOutdoor spaces

Bulldog Cottage
FamilyLocationAccuracy

Stunning 2 Bedroom Stone Cottage, North York Moors
FamilyLocationNearby

Dunnwell Lodge, North Yorkshire
LocationFamilyOutdoor spaces

Lovely family home with a beautiful view
LocationValueGetting around

The Dovecote in Rosedale
FamilyValueParking
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
- Scarborough Beach
- National Railway Museum
- Teesside University
- The Deep
- Peasholm Park
- Bridlington Spa
- Durham University
- First Direct Arena





