
House holiday rentals in Helmsley
Find and book unique houses on Airbnb
Top-rated house rentals in Helmsley
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

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!

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.

Little Hillside
A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to go off grid, listen to the wildlife and enjoy the beautiful countryside. York is 20 miles away with countless tourist attractions and less than 10 minutes drive is the pretty market town of Helmsley 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.

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.

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.

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.

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.

Oakforge Cottage, a spacious home from home.
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.

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.

Rural homely cottage in North York Moors
Cosy cottage located in the North York Moors National Park with gorgeous big skies! A super base for exploring castles, abbeys, villages and the Heritage coast. Spoilt for choice in eateries from great local pubs to Michelin starred restaurants all with a 10 mile radius. Many guests comment on how peaceful and calm their stay has been. My place is good for couples, solo adventurers, families with children and pets (one, well behaved dog only).

The Pavilion at Beck House, Bishop Thornton
Nestled peacefully in the woodlands of Bishop Thornton, Harrogate, The Pavilion is a newly converted 2 bedroom tranquil retreat. Accessed via a private road, The Pavilion, situated on the Nidderdale Way, offers a luxurious, warm and cosy stay for those seeking a relaxing break in the Yorkshire Dales.
Popular amenities for house rentals in Helmsley
House rentals with a pool

The Hideaway with Private Pool and Stunning Views

Silversands House at The Bay Filey - sea views

Beautiful Dales Cottages with Pool, Hot-tub & Gym

Cottage sleeps 5 with indoor swimming pool

The Elliott Suite @ Southfield Barton-UponHumber

Salty Kisses, The Bay, Filey

Charming 4-bedroom home at Broughton Sanctuary

Chestnut Cottage, Killerby Old Hall
Weekly house rentals

Luxury Yorkshire Barn Conversion

Charming 19th Century property

The Mill House, spacious barn conversion

Heather Cottage On't Cobbles

Lovely family home with a beautiful view

Spring Cottage, Husthwaite

The Town House

Stunning 2 Bedroom Stone Cottage, North York Moors
Private house rentals

Vinery Farm - sleeps 10

Dunnwell Lodge, North Yorkshire

Stylish York Retreat | Jacuzzi bath

The Town House @ College Square

The Barn at Noelle's Cottages

Cowslip Retreat

Charming cottage

Old Stone Cottage
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 £135 per night before taxes and fees

Verified guest reviews
Over 480 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Helmsley holiday rentals include wifi 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!
Destinations to explore
- Durham Holiday rentals
- Elgin Holiday rentals
- London Holiday rentals
- Sea of the Hebrides Holiday rentals
- Thames River Holiday rentals
- Amsterdam Holiday rentals
- South West Holiday rentals
- Inner London Holiday rentals
- Dublin Holiday rentals
- South London Holiday rentals
- Yorkshire Holiday rentals
- Central London Holiday rentals
- Yorkshire Dales National Park
- yorkshire dales
- Flamingo Land Resort
- First Direct Arena
- Fountains Abbey
- Harewood House
- York Castle Museum
- Filey Beach
- Durham Cathedral
- National Railway Museum
- Bempton Cliffs
- Yorkshire Coast
- Royal Armouries Museum
- Scarborough Open Air Theatre
- Temple Newsam Park
- The Piece Hall
- York University
- Scarborough Beach
- Yorkshire Sculpture Park
- York Minster
- The Deep
- Teesside University
- University of Leeds
- Peasholm Park





