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

Total holiday rentals
Explore 10 holiday rentals in Helmsley

Nightly prices starting at
Helmsley holiday rentals start at $375 NZD per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
10 of Helmsley holiday 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.
LocationFamilyBathroom

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!
ValueFamilyWalkability

Luxury Country Cottage Hot Tub Spa Retreat | York
Snowdrop Cottage is a luxurious 5★ retreat nestled in the picturesque village of Welburn, surrounded by the breathtaking Howardian Hills, just minutes from the iconic Castle Howard, the city of York and the Yorkshire coastline. An idyllic escape, this beautifully styled boutique cottage features a private garden spa & hot tub, cosy log burner & romantic four-poster king-size bed - the perfect setting for couples, families and dog walkers to relax, reconnect and explore the Yorkshire countryside.
FamilyLocationKitchen

The Sanctuary, Pet friendly
Relax with the whole family at this peaceful place to stay. Beautiful village residence but only 4 miles from stunning historic York with easy public transport access. Bring your pet too, they have indoor and outdoor space and wonderful country walks in the local area. Enjoy our sunroom, a cosy space to eat in Summer or Autumn. Our local pub is on the doorstep serving excellent home cooked meals or a take away Sunday lunch. With 2 parking spaces and secure lock up lock up for mountain bikes.
LocationValueCheckout

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.
FamilyLocationPool

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.
FamilyLocationParking

Spinney Cottage, Pateley Bridge
Spinney Cottage is a beautifully restored home located just outside the town of Pateley Bridge in Nidderdale, a short drive from the Yorkshire Dales and Harrogate. Built in 1883 and full of characterful features such as woodburning stove and exposed stone walls, the Cottage is very well equipped with BBQ, firepit, and outdoor seating. Set in 4 acres of gardens and woodland, guests can make the most of our peaceful location. Ideal for walkers, cyclists and those looking for a calming retreat.
FamilyLocationBreakfast

The Old Post Office pretty village 20min from York
The Old Post Office, providing a lovely 3 bedroom character suite, with private, off road parking and a sunny private courtyard to enjoy outside eating and relaxation.. Situated in the beautiful village of Alne, 10 miles from York and access to Harrogate, the Dales, the North York Moors and the Coast. The Area has just been awarded "one of the Best Places to Live in the UK" by The Sunday Times. Stylish, Egyptian cotton bedding on all beds and providing everything you will want for your stay.
FamilyLocationCleanliness

Stunning deluxe space, mezzanine floor, great view
About this space. Tamworth This is a stunning, stylish cottage with a steel mezzanine platform with a super king size bed. The floor to roof glass front faces West so stunning sunsets are a feature with views out to paddocks with horses and hens. Walk in shower room with door opens to black splash surround and a copper colour rainfall shower and black sink, loo and floor. Striped bamboo flooring throughout. Pitched roof with windows so when lying in bed you can see the stars at night.
LocationValueAccuracy

Short stroll to pubs, cafés & shops. Free Parking
Enjoy a clean and comfortable, cosy yet spacious, experience at this peacefully located holiday home. Just a very short stroll from Pickering town centre where you’ll be spoilt for choice with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking or free parking permit for Eastgate car park which is less than 300 meters away.
LocationValueBathroom

The Shed, Hovingham, York
An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.
ValueFamilyCleanliness

Heather Cottage On't Cobbles
Nestled within the idyllic village of Haworth at the heart of Bronte Country; Our little holiday cottage stands proud at the very top of the historical cobbled street. With exposed original features and rich colour schemes drawn from the picturesque surroundings of the Haworth moors (where Cathy and Heathcliffe ran wild!) guests can expect to be transported to an earlier time whilst still benefiting from the luxury of modern-day amenities.
LocationFamilyBathroom
Popular amenities for Helmsley house rentals
House rentals with a pool

North Wing of Langton Hall - Grade 2 listed
FamilyValueBackyard

The Elliott Suite @ Southfield Barton-UponHumber
ValueFamilyDecor

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

Salty Kisses, The Bay, Filey
LocationValueSleep quality

Brand new 2021 ABI WINDERMERE STATIC Cedar 1
ValueFamilyGetting around

The Hideaway with Private Pool Sleeps 2
FamilyValueDecor

One bedroomed cottage with swimming pool.
LocationFamilyWi-Fi

The Stables - Birdforth Hall Holiday Cottages
FamilyValueAmenities
Weekly house rentals

Explore North Yorkshire. Large, stylish farmhouse
ValueLocationHot tub

Sunny Bank Snug garden retreat near Hebden Bridge
ValueLocationDecor

Stylish spacious country cottage
LocationFamilyCondition

Stationmaster's Cottage
ValueLocationBarbecue

The Salt House Cottage, Pilmoor
LocationValueLaundry

Country Manor House - Nr Richmond North Yorkshire
LocationValueNearby

Beautiful, quiet and private historic Coach House
LocationFamilyBeach

Luxury Cottage | Hot Tub | Heart of Helmsley
FamilyLocationPets
Private house rentals

Bulldog Cottage
LocationSleep qualityNearby

Stunning 2 Bedroom Stone Cottage, North York Moors
LocationFamilyLayout

Cowslip Retreat
FamilyLocationSleep quality

Bank House
LocationValueGetting around

Charming Yorkshire Cottage near The Coast & York
LocationAmenitiesCleanliness

NEW! Cosy Stone Cottage With Free Parking & Wifi
LocationKitchenCleanliness

Town Gate Cottage
LocationFamilyTV

The Barn at Noelle's Cottages
ValueLocationEV charging
Destinations to explore
- Yorkshire Dales National Park
- yorkshire dales
- Yorkshire Coast
- Filey Beach
- Bempton Cliffs
- Harewood House
- Fountains Abbey
- York Castle Museum
- Bramham Park
- Temple Newsam Park
- York University
- York Minster
- Scarborough Beach
- Yorkshire Sculpture Park
- Teesside University
- The Deep
- Peasholm Park
- Bridlington Spa
- First Direct Arena
- Blue Dolphin Holiday Park - Haven
- Malham Cove
- Richmond Castle
- Lightwater Valley
- The Bowes Museum





