Holiday rentals in Helmsley

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Top-rated holiday rentals in Helmsley

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Flat in Gilling East

4.95 out of 5 average rating, 125 reviews

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.

12–19 Dec

€ 107 per night
Guest favourite

Farm stay in Pockley

4.97 out of 5 average rating, 107 reviews

Couple's Bothy near Helmsley in the National Park

Take it easy at this unique and tranquil getaway. Our converted barn offers a cosy, self-catering retreat for two on our remote, but accessible farm in the North York Moors National Park. The Bothy is a self-contained, open space providing king sized bed, ensuite, kitchen, sitting area, outside terrace sun trap & free WiFi. The Bothy has been completed to an exceptionally high standard combining beautiful detailing and practicality. We are blessed with a wonderful location for walking & cycling.

14–21 Aug

€ 123 per night
Guest favourite

Train in Helmsley

4.88 out of 5 average rating, 172 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 !

2–9 Jan

€ 193 per night

Popular amenities for Helmsley holiday rentals

Stay near Helmsley's top sights

Helmsley Castle25 locals recommend
National Centre for Birds of Prey14 locals recommend
Helmsley Walled Garden21 locals recommend
Feversham Arms Hotel & Verbena Spa9 locals recommend
The Feathers Hotel8 locals recommend
The Black Swan Hotel6 locals recommend

Other great holiday rentals in Helmsley

Guest favourite

Apartment in North Yorkshire

4.98 out of 5 average rating, 216 reviews

2 Chiltern Place Malton-Stylish boutique apartment

5–12 Mar

€ 116 per night
Guest favourite

Guest suite in Nunnington

4.87 out of 5 average rating, 174 reviews

Renovated 16th century haven in North Yorks Moors

9–16 Feb

€ 91 per night
Guest favourite

Barn in Aislaby, Pickering

4.96 out of 5 average rating, 221 reviews

Stunning views, 4 acres, dog friendly, Yorkshire

19–26 Feb

€ 196 per night
Guest favourite

Cottage in Kirkbymoorside

4.87 out of 5 average rating, 325 reviews

Fuchsia Cottage- a cosy getaway

14–21 Nov

€ 91 per night
Guest favourite

Cottage in Sessay

4.95 out of 5 average rating, 216 reviews

The Cobbler's Cottage

31 Jul – 7 Aug

€ 114 per night
Guest favourite

Barn in Aislaby

4.97 out of 5 average rating, 193 reviews

Hidden Gem On The Edge Of The North York Moors

14–21 Sep

€ 107 per night
Guest favourite

Barn in Kirby Wiske

4.98 out of 5 average rating, 183 reviews

An entire barn conversion in stunning location

21–28 Oct

€ 133 per night
Guest favourite

Cottage in East End

4.99 out of 5 average rating, 237 reviews

The Owlets, Ampleforth

27 Jan – 3 Feb

€ 178 per night
Guest favourite

Home in Helmsley

4.93 out of 5 average rating, 111 reviews

Holiday at 44 - wonderfully situated for all

6–13 Dec

€ 254 per night
Guest favourite

Tiny home in Newton-on-Rawcliffe

4.99 out of 5 average rating, 178 reviews

The Hide NYM National Park Cosy Cabin with hot tub

2–9 Dec

€ 123 per night
Guest favourite

Cottage in Helmsley

4.83 out of 5 average rating, 12 reviews

Holiday cottage in lovely Helmsley

9–16 Nov

€ 123 per night
Guest favourite

Home in Hovingham

4.9 out of 5 average rating, 81 reviews

The Shed, Hovingham, York

21–28 Feb

€ 137 per night

Quick stats about holiday rentals in Helmsley

Total rentals

50 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1.7K reviews

Nightly prices starting at

€ 55 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Helmsley