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Family-friendly holiday rentals in Helmsley

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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, 174 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 !

29 Jan – 5 Feb

€ 195 per night

Guest favourite

Farm stay in Boltby near Thirsk

4.96 out of 5 average rating, 300 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

17–24 Mar

€ 124 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!

3–10 Oct

€ 154 per night

Guest favourite

Tiny home in North Yorkshire

5.0 out of 5 average rating, 297 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.

21–28 Nov

€ 135 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.

9–16 Dec

€ 120 per night

Guest favourite

Flat in North Yorkshire

4.99 out of 5 average rating, 170 reviews

Private Garden Apartment With Off Road Parking.

Spacious, relaxing, south facing, Georgian apartment with private garden. Located in the heart of Scarborough's historical Old Town. Ensuite bedroom with super king bed (2 singles upon request). Galley kitchen with full cooking facilities. Secure off road parking for one vehicle (enquire if very large). Wifi, TV, DVDs, books & games galore. 5 mins walk to beach, harbour, castle & local market. 15 min walk to town centre shopping & train station. Check in from 3pm-10pm.

17–24 Jul

€ 165 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.

3–10 Feb

€ 100 per night

Guest favourite

Cottage in Helmsley

4.91 out of 5 average rating, 134 reviews

Cliff Stud Retreat, Helmsley, Frankel Cottage

Our 3 bedroom cottage has stunning countryside views due to its location. With a wood burner and cosy decor it's the perfect bolt hole for couple and families alike. Frankel cottage sleeps up to 5 guests (it’s advised 4 adults maximum) and has a fully equipped kitchen inc wm/microwave. The bathroom fully refurbished (shower/bath)is located downstairs. The cottage is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

18–25 Dec

€ 245 per night

Guest favourite

Home in North Yorkshire

4.89 out of 5 average rating, 177 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).

29 Nov – 6 Dec

€ 144 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

8–15 Oct

€ 151 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.

29 Sep – 6 Oct

€ 100 per night

Guest favourite

Cottage in Osmotherley

4.98 out of 5 average rating, 197 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.

6–13 Nov

€ 141 per night

Holiday rentals for every style

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Quaint homes, peaceful surroundings

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Stylish accommodation 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 North Yorkshire

4.94 out of 5 average rating, 160 reviews

Alice's Cottage - Hot tub in private garden

30 Jun – 5 Jul

€ 189 per night

Guest favourite

Cabin in Huggate

4.99 out of 5 average rating, 183 reviews

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

5–12 Jan

€ 172 per night

Cottage in North Yorkshire

4.84 out of 5 average rating, 109 reviews

Cheeky Chicken Cottage, York, (Jacuzzi Hot Tub)

2–9 Nov

€ 198 per night

Guest favourite

Home in Sutton-on-the-Forest

4.93 out of 5 average rating, 115 reviews

Large detached house near York

10–17 Apr

€ 454 per night

Guest favourite

Cottage in Fylingthorpe

4.97 out of 5 average rating, 355 reviews

Hazel Cottage nestled twixt coast and Moorland

4–11 Sep

€ 207 per night

Guest favourite

Barn in Ripponden

4.95 out of 5 average rating, 403 reviews

NEW BARN CONVERSION WITH PRIVATE HOT TUB

6–13 Apr

€ 179 per night

Guest favourite

Cottage in Loftus

4.9 out of 5 average rating, 189 reviews

Rambling Rose Cottage, near Staithes

17–24 Mar

€ 196 per night

Guest favourite

Cottage in Hebden Bridge

4.94 out of 5 average rating, 123 reviews

Detached Cottage,HebdenBridge on Pennine Way

17–24 Apr

€ 131 per night

Family- and pet-friendly home rentals

Guest favourite

Cottage in Great Ayton

4.96 out of 5 average rating, 335 reviews

Spacious barn conversion in North Yorkshire

Guest favourite

Flat in Ripon

4.9 out of 5 average rating, 193 reviews

The Old Cottages,Grade2 listed with Gated Parking

27 Jun – 4 Jul

€ 151 per night

Guest favourite

Cottage in East Riding of Yorkshire

4.97 out of 5 average rating, 328 reviews

The Hayloft at Bainton - 2 bedroom cottage.

19–26 Jul

€ 141 per night

Guest favourite

Cottage in West Ayton

4.94 out of 5 average rating, 123 reviews

Cottage near Scarborough fab country views parking

7–14 Apr

€ 164 per night

Guest favourite

Tiny home in Ripponden

5.0 out of 5 average rating, 269 reviews

Cosy, peaceful woodland retreat

18–25 Oct

€ 87 per night

Guest favourite

Cabin in Ripponden

4.98 out of 5 average rating, 285 reviews

Cosy Log cabin in beautiful Yorkshire countryside

28 Mar – 4 Apr

€ 113 per night

Guest favourite

Home in West Yorkshire

4.96 out of 5 average rating, 595 reviews

The Cow Shed,Sandbeck Farm,Wetherby

14–21 Nov

€ 115 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

28 Nov – 5 Dec

€ 515 per night

Family-friendly home rentals with a pool

Guest favourite

Apartment in North Yorkshire

4.93 out of 5 average rating, 160 reviews

Yorkshire Coast Retreat The Bay Filey Wifi Pets

18–25 Mar

€ 106 per night

Guest favourite

Flat in North Yorkshire

4.86 out of 5 average rating, 143 reviews

Filey Bay Cove The Bay Filey Wifi Pets Pool Gym

24–31 Aug

€ 133 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

4–11 Oct

€ 175 per night

Cottage in Holmfirth

4.9 out of 5 average rating, 122 reviews

Mallard - with private hot-tub and pool options

22–29 Sep

€ 97 per night

Guest favourite

Home in The Bay

4.97 out of 5 average rating, 120 reviews

Sandy Toes, The Bay, Filey

13–20 Sep

€ 140 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

20–25 May

€ 144 per night

Guest favourite

Cottage in Filey

4.98 out of 5 average rating, 62 reviews

Bumblebee Cottage Filey: sea views, dog friendly

15–22 Oct

€ 197 per night

Guest favourite

Cottage in Primrose Valley

4.93 out of 5 average rating, 14 reviews

Puddle Duck Cottage - Sleeps 4, The Bay Filey

23–30 Nov

€ 104 per night

Quick stats about holiday 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
€ 84 before taxes and fees

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