
Family-friendly holiday rentals in Helmsley
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Helmsley
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Fairfax View - delightful annexe cottage, Gilling
Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

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.

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.

Delightful Shepherd’s Hut with creature comforts
Stay in the heart of nature in our unique hand-crafted Shepherd’s Hut combining rural simplicity with all the comforts you need to make your stay enjoyable and memorable. Situated in the heart of the Pennines, ‘The Spot’ is immersed in nature but within walking distance of rail/bus/canal access as well as the quirky town of Hebden Bridge. The perfect base for exploring the beautiful rolling hills and valleys - on foot or on wheels - or just switch off and relax on site - alpacas optional!

Cosy modern home in Ampleforth village
No.6 is a lovely property in the beautiful village of Ampleforth. A fantastic location to head off into the National Parks or the coast. Ampleforth enjoys 2 great pubs, gorgeous Coffee Shop/cafe, village shop & Post Office ALL ONLY 5 MINS WALK. The pretty market town of Helmsley 4 miles & enjoy the facilities at St Alban Sports Centre with indoor pool & gym less 1 mile from village. 1 NIGHT STAYS CARRY SUPP OF £20. We also have 3 bed detached house (sleeps 6) in Ampleforth

Kilburn Chicken Cottage
Opened in 2018, dog-friendly Kilburn Chicken Cottage has been hosting guests from all over the world. With one of the highest Airbnb ratings in the area, parents and children alike have loved coming to stay to look after their own flock of hens. This 3 bedroom cottage is situated in the beautiful North Yorkshire village of Kilburn, with fast EV charging in Thirsk nearby. You're spoilt for choice when it comes to great views, great food and entertaining hens.

Mill House Annex, Oldstead
This bolthole has been lovingly refurbished to a high standard throughout, providing guests with a comfortable and cosy home-from-home. There is a spacious bedroom with a king-size bed, a modern bathroom fitted with underfloor heating and a sperate bath and shower. The living room has a cosy log fire and large dining table. The kitchen is well appointed and kitted out to meet all your culinary needs. Take it easy at this unique and tranquil getaway.

Stunning views, 4 acres, dog friendly, Yorkshire
Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

The Flat @ 2 Castlegate
Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

Cliff Stud Retreat, Helmsley - Cecil Cottage
Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set within the 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.

Garden Cottage - Peaceful in the Heart of Helmsley
A Unique Self-Catering Experience ! Stay in your own private luxury Home-from-Home private cottage, attached to our 1560-Built property opposite the Market square. Your own private entrance leads into your own Dining Room and Kitchenette area which leads into your own large separate Lounge. A well-appointed Shower Room is situated on the ground floor. Upstairs is a large Bedroom with fitted wardrobes and TV.
Popular amenities for Helmsley family-friendly rentals
Family-friendly home rentals with a hot tub

La Fenetre Holiday Cottage

The Hut in the Wild

Stunning rural shepherds hut

Large detached house near York

Charming farm based cottage with hot tub/sauna

Storey Corner - Where memories are made

Cozy Stay at Animal Sanctuary

The Highlander
Family- and pet-friendly home rentals

Unique 18thC Yorks Dales Silk Weavers’ mill house.

The Little House Peaceful & self-contained

Farm Cottage with Stunning Views.

The Studio, Boltby near Thirsk. Wifi. Great views.

Glamping Pod w BBQ & Onsite Café-Near Durham Dales

The Barn

Cosy Country Cottage Sleeps 4

Idyllic cottage by the River Tees, North Yorkshire
Family-friendly home rentals with a pool

Sandy Toes, The Bay, Filey

Secret of Eden Beach House - Pet friendly WiFi E.V

2 bed holiday lodge

The Elliott Suite @ Southfield Barton-UponHumber

The Tree Cabin

Historic 18th Hussars Cottage with a Modern twist

Hot Tub Pet Friendly York

Luxury Cabin with Hot Tub & Spa Facilities
Quick stats about holiday rentals that are family-friendly in Helmsley

Total holiday rentals
Explore 40 holiday rentals in Helmsley

Nightly prices starting at
Helmsley holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 1,470 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Helmsley holiday rentals include wifi access

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

4.8 Average rating
Helmsley stays are highly rated by guests – averaging 4.8 out of 5!
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- Yorkshire Dales National Park
- Robin Hood’s Bay
- Flamingo Land Resort
- yorkshire dales
- Harewood House
- Fountains Abbey
- York Castle Museum
- Durham Cathedral
- National Railway Museum
- Royal Armouries Museum
- Yorkshire Coast
- The Piece Hall
- Scarborough Open Air Theatre
- Temple Newsam Park
- Semer Water
- York University
- Saltburn Beach
- Bramham Park
- Bempton Cliffs
- Yorkshire Sculpture Park
- The Bowes Museum
- Malham Cove
- Durham University
- York Minster




