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Family-friendly vacation 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.

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Train in Helmsley

4.88 out of 5 average rating, 175 reviews

Unique Railway Carriage - In the Heart of Helmsley

Helmsley Railway Carriage…..A Special Experience ! Our 1887, 3rd Class Victorian Railway Carriage converted to 5* standards. With all the facilities of a self-catering property including a full kitchen and lounge/dining area including a welcome pack of essentials included in your rate. In service to 1905, running between York & Scarborough, the Carriage ended up at Helmsley Railway Station, then brought to our property in that year ! The UK's oldest & unusual Train Carriage accommodation !

Apr. 3 – 10

$282 CAD per night

Guest favourite

Farm stay in Boltby near Thirsk

4.96 out of 5 average rating, 301 reviews

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

A studio flat, at Willow Tree Cottage, in rural Boltby. This one roomed apartment has everything you need - a fully fitted kitchen, woodburning stove ensuite shower room, own garden & garden room, double, single bed & Z bed for second child. Wonderful views. Peaceful. Free Wi-fi. 5 miles to Thirsk. Children free. Suitable for 3 adults or a family of 4 (2 adults & 2 children). For children under 16 contact me for a special offer. Good walking, cycling, nature, star gazing, horse riding

Dec. 20 – 27

$178 CAD per night

Guest favourite

Apartment in Ripon

4.9 out of 5 average rating, 193 reviews

The Old Cottages,Grade2 listed with Gated Parking

Fully modernised, grade 2 Listed Ground Floor one bed Cottage in the heart of The Cathedral City of Ripon. Private Gated Car Park & lovely Walled Courtyard Garden ... Stunning open plan Kitchen with Huge Fireplace & Log Burner. Dinning area in front of Log burner and Sitting Room area of to one side. Secluded Bedroom and En suite Bathroom up two stairs and through an Oak door …. Free Unlimited Fast WiFi and Samsung Smart HD TV. All doors and Gates are Code access which Saves Sharing a Key!

Jun. 27 – Jul. 4

$221 CAD per night

Guest favourite

Loft in Masham

4.91 out of 5 average rating, 315 reviews

The Old Masham Library - Grade 2 listed

The Grade 2 listed Old Library, Masham sits on the corner of the principle approach in to the Market Square from Swinton. Built in 1856 it originally served as the Mechanic Institute of then Mashamshire. It was designed by the respected William Perkin of Perkin and Backhouse of Leeds in Victorian Italianate style. In 2017-18 its internal was redesigned and fully refurbished by Langton Holdings Ltd. On the side of the building is 7kw EV charging by podpoint so be sure to download the app!

Jan. 20 – 27

$223 CAD per night

Guest favourite

Tiny homes in North Yorkshire

5.0 out of 5 average rating, 298 reviews

1855 Wash House, Town Centre Studio Cottage

The 1855 Wash House is a studio cottage, located within a minutes walk from Skipton High Street. It is on one level apart from one step down into the kitchen. The studio is situated at the rear of a Victorian terrace within the owners garden. There is an outdoor flagged area for guests with sheltered seating for 2. There is a permit parking space at the front of the cottage. Several early morning opening cafes are close by and Marks and Spencers Simply food is just around the corner.

Nov. 22 – 29

$195 CAD per night

Guest favourite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Braecote is a peaceful, warm, and welcoming cottage in the picture perfect village of Coxwold. With wide grass verges, honey coloured stone houses and a traditional country pub just up the road, Coxwold is one of the prettiest villages in North Yorkshire. York, Harrogate, Helmsley and Malton are close by, the North York Moors, Yorkshire Dales and east coast all within easy reach. Newburgh Priory is just up the road and Michelin starred Black Swan at Oldstead a short drive away.

Jan. 13 – 20

$173 CAD per night

Guest favourite

Guest suite in Sutton-on-the-Forest

5.0 out of 5 average rating, 224 reviews

Countryside location near to York

Nestled in the countryside just outside York, 'The Kennel' is a relaxing and peaceful retreat. This small but perfectly formed self-contained annex is set in three acres of newly planted woodland in which you can often see the Barn, Tawny and Little Owls visiting to be fed from the feeding posts, garden, small orchard, wildlife pond and apiary housing up to 8 beehives which provide us with some delicious honey. To the rear of the property is a Whisky and Gin Distillery.

Jan. 5 – 12

$143 CAD per night

Cottage in Helmsley

4.87 out of 5 average rating, 116 reviews

Cliff Stud Retreat, Helmsley - Cecil Cottage

Cecil cottage is A three bedroom cozy cottage set within the 220 acres Cliff Stud retreat estate, 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. The bathroom has a shower/bath & is fully refurbished.The cottage boasts it's own garden with fruit trees and is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

Sep. 8 – 15

$358 CAD per night

Guest favourite

Home in North Yorkshire

4.89 out of 5 average rating, 178 reviews

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).

Jan. 14 – 21

$207 CAD per night

Guest favourite

Barn in York

4.99 out of 5 average rating, 454 reviews

Tanyard Barn, Whixley - North Yorkshire

We are located between Harrogate and York. Tanyard Barn is a self contained 2 storey property. Located in the picturesque village of Whixley, North Yorkshire. Excellent transport links by train, road or bus to nearby York, Knaresborough and Harrogate. 2 miles from the A1 allows you to explore the beautiful countryside of North Yorkshire, The Dales, and the coast. Village shop and pub

Oct. 4 – 11

$219 CAD per night

Guest favourite

Guest suite in Ampleforth

4.93 out of 5 average rating, 212 reviews

Lovely self-contained hillside village Annexe

We are following government advice: if movement restrictions are reintroduced, we will offer a full refund for your stay. We are committed to following AirBnB's enhanced cleaning and disinfecting protocol. On arrival, guests check themselves into completely self-contained accommodation. We will do everything in our power to ensure the safety and comfort of our guests.

Jun. 5 – 12

$144 CAD per night

Guest favourite

Cottage in Osmotherley

4.98 out of 5 average rating, 198 reviews

Stanley Cottage, in the heart of Osmotherley

Traditional, cosy old weavers cottage with all modern facilities. In the heart of the village of Osmotherley, with great access to the North York Moors for walkers, dog owners, cyclists and families enjoying good food. Visit our website: stanleycottageosmotherley . co . uk Please note, if covid restrictions prevent your stay then a refund would be paid.

Nov. 30 – Dec. 7

$204 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Helmsley family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Shipton

4.98 out of 5 average rating, 217 reviews

The Stables with Jacuzzi & tennis court

Nov. 9 – 16

$429 CAD per night

Guest favourite

Home in North Yorkshire

4.94 out of 5 average rating, 160 reviews

Alice's Cottage - Hot tub in private garden

Jun. 30 – Jul. 5

$273 CAD per night

Guest favourite

Cabin in Huggate

4.99 out of 5 average rating, 184 reviews

1 Bedroom Lodge (Hot Tub) - On top of the Wolds

Nov. 28 – Dec. 5

$251 CAD per night

Cottage in North Yorkshire

4.84 out of 5 average rating, 109 reviews

Cheeky Chicken Cottage, York, (Jacuzzi Hot Tub)

Oct. 31 – Nov. 7

$291 CAD per night

Guest favourite

Home in Sutton-on-the-Forest

4.93 out of 5 average rating, 115 reviews

Large detached house near York

Apr. 10 – 17

$656 CAD per night

Guest favourite

Cottage in Fylingthorpe

4.97 out of 5 average rating, 355 reviews

Hazel Cottage nestled twixt coast and Moorland

Sep. 7 – 14

$299 CAD per night

Guest favourite

Barn in Ripponden

4.95 out of 5 average rating, 404 reviews

NEW BARN CONVERSION WITH PRIVATE HOT TUB

Apr. 6 – 13

$258 CAD per night

Guest favourite

Cottage in Loftus

4.9 out of 5 average rating, 189 reviews

Rambling Rose Cottage, near Staithes

Mar. 31 – Apr. 7

$281 CAD per night

Family- and pet-friendly home rentals

Guest favourite

Cottage in West Ayton

4.94 out of 5 average rating, 123 reviews

Cottage near Scarborough fab country views parking

Jun. 14 – 21

$226 CAD per night

Guest favourite

Cottage in East Riding of Yorkshire

4.97 out of 5 average rating, 329 reviews

The Hayloft at Bainton - 2 bedroom cottage.

Apr. 19 – 26

$204 CAD per night

Guest favourite

Cottage in Great Ayton

4.96 out of 5 average rating, 336 reviews

Spacious barn conversion in North Yorkshire

Guest favourite

Tiny homes in Ripponden

5.0 out of 5 average rating, 269 reviews

Cosy, peaceful woodland retreat

Mar. 8 – 15

$125 CAD per night

Guest favourite

Barn in Sutton on the Forest

5.0 out of 5 average rating, 112 reviews

Luxury Barn conversion Nr York , family & groups

Mar. 19 – 26

$745 CAD per night

Guest favourite

Cabin in Ripponden

4.98 out of 5 average rating, 287 reviews

Cosy Log cabin in beautiful Yorkshire countryside

Nov. 28 – Dec. 5

$165 CAD per night

Guest favourite

Home in West Yorkshire

4.96 out of 5 average rating, 596 reviews

The Cow Shed,Sandbeck Farm,Wetherby

Oct. 28 – Nov. 4

$166 CAD per night

Guest favourite

Apartment in North Yorkshire

4.96 out of 5 average rating, 217 reviews

17a Grape Lane, Whitby

Jan. 7 – 14

$221 CAD per night

Family-friendly home rentals with a pool

Guest favourite

Condo in North Yorkshire

4.93 out of 5 average rating, 160 reviews

Yorkshire Coast Retreat The Bay Filey Wifi Pets

Jan. 30 – Feb. 6

$153 CAD per night

Guest favourite

Apartment in North Yorkshire

4.86 out of 5 average rating, 143 reviews

Filey Bay Cove The Bay Filey Wifi Pets Pool Gym

Aug. 24 – 31

$192 CAD per night

Guest favourite

Cottage in The Bay North Yorkshire

4.99 out of 5 average rating, 135 reviews

Relax at lovely Collie Cottage, The Bay Filey

Dec. 20 – 27

$276 CAD per night

Guest favourite

Home in The Bay

4.97 out of 5 average rating, 120 reviews

Sandy Toes, The Bay, Filey

Apr. 7 – 14

$351 CAD per night

Guest favourite

Cottage in Filey

4.98 out of 5 average rating, 63 reviews

Bumblebee Cottage Filey: sea views, dog friendly

Nov. 22 – 29

$196 CAD per night

Guest favourite

Cottage in North Yorkshire

5.0 out of 5 average rating, 95 reviews

Rodgers Retreat The Bay Filey YO14 9GL See Map

May 20 – 25

$209 CAD per night

Guest favourite

Cottage in Filey

4.95 out of 5 average rating, 41 reviews

Rockpool cottage The Bay Filey, 3 bed sleeps 6

Jan. 29 – Feb. 5

$195 CAD per night

Cottage in Filey

4.81 out of 5 average rating, 37 reviews

Sea Urchins Cottage with sea view at The Bay Filey

Nov. 11 – 18

$208 CAD per night

Quick stats about vacation rentals that are family-friendly in Helmsley

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
1.2K reviews
Nightly prices starting at
$123 CAD before taxes and fees

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