Walking holidays with Where2Walk

You're never far from a breathtaking walk in Yorkshire and so we've partnered with Where2Walk to bring you over 500 cottages in Yorkshire's most stunning locations so you can enjoy the best of what Yorkshire has to offer on foot. We've joined up with Jonathon Smith of Where2Walk, a local expert who has been walking the footpaths of Yorkshire all his life (you can usually catch him somewhere with his faithful companion Mist the Border Collie!). Here he shares his top tips to making the most of your stay in Yorkshire. 

The benefits of walking in Yorkshire:

  • Variety of landscape that is within an easy drive from any of the Yorkshire cottages: rolling hills, high moors, interesting valleys, riverside walking, pretty villages, market towns
  • Empty: there are few people out on the footpaths compared to somewhere like the Lake District so a real sense of space, exploration and emptiness (in a positive way)
  • Paths are excellent and in good condition, not over eroded
  • History: Abbey walks, stone age settlements, lead/iron mining from the 19th century, smugglers/coastal, geological differences including limestone country.
  • Some excellent mountains in the Dales including the ‘Dales 30 ‘
  • In addition it is of course healthy and good fun!

How to make the most of your walking holiday:

  • Take a navigation course, learn to read a map and use a compass and therefore enjoy walking further afield (special rates available for Ingrid Flute customers)
  • Hire an expert guide for a day to show you the best places to walk or take you safely but further than you would normally go
  • Challenge yourself and climb the mountains of the Dales 30. 

The cottages below are our favourites for walking, with many close to famous walking routes or with beautiful trails right from the doorstep. Our team would be happy to offer any recommendations for places to stay, routes to meet your abilities or suggest great pubs along the routes! Call us on 01947 600700.



View more and filter search
511 Properties found
Back to list view

Leyburn, Yorkshire Dales

DS300

(No dates selected)

£1392 - £2305
per week
From £1,054 for a 3-night stay
  • 5 Star Gold
  • This spacious detached luxury property sleeping six has been furnished and equipped to the highest specification. With a hot tub in it's stunning designer garden it is the perfect escape in the Yorkshire Dales.
  • 6 Guests
  • 3 Bedrooms
  • No Pets
  • 3 Bathrooms
  • WiFi
  • Garden
  • Private parking
  • Hot tub
  • Open fire or woodburner
  • Beach 40 miles
  • Pub 0.25 miles

Barnard Castle, Teesdale & Durham Dales

DS952

(No dates selected)

£2540 - £5540
per week
From £1,915 for a 3-night stay
  • 5 Star Gold
  • This spacious stylishly furnished detached stone farmhouse surrounded by rolling countryside with 2 reception rooms and a playroom for the children.
  • 14 Guests
  • 7 Bedrooms
  • No Pets
  • 5 Bathrooms
  • WiFi
  • Garden
  • Private parking
  • Open fire or woodburner
  • Beach 33 miles
  • Pub 0.5 miles

Leyburn, Yorkshire Dales

DS913

(No dates selected)

£766 - £1224
per week
From £585 for a 3-night stay
  • 5 Star Gold
  • A stunning barn conversion nestled in a small village in the Yorkshire Dales with a wood fired hot tub and fantastic views over Wensleydale.
  • 4 Guests
  • 2 Bedrooms
  • 2 Pets
  • 2 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Hot tub
  • Beach 50 miles
  • Pub 0.5 miles

Gunnerside, Yorkshire Dales

DS097

(No dates selected)

£852 - £1791
per week
From £649 for a 3-night stay
  • 5 Star
  • This spacious converted stone barn sleeping up to eight has been furnished and equipped to a very high standard. Stunning panoramic views over the valley.
  • 6 Guests
  • 3 Bedrooms
  • 2 Pets
  • 2 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Open fire or woodburner
  • Games room
  • Beach 57 miles
  • Pub 0.8 miles

Aysgarth, Yorkshire Dales

DS936

(No dates selected)

£1519 - £2555
per week
From £1,149 for a 3-night stay
  • 5 Star
  • This luxurious, newly renovated cottage, set in the charming Wensleydale village of Aysgarth in the Yorkshire Dales is full of charm and features state of the art technology, along with a wood burner and hot tub.
  • 7 Guests
  • 5 Bedrooms
  • 2 Pets
  • 3 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Hot tub
  • Open fire or woodburner
  • Beach 51 miles
  • Pub 0.3 miles

Whitby, Whitby

W445

(No dates selected)

£540 - £1055
per week
From £415 for a 3-night stay
  • 5 Star
  • A modern and luxurious 5 star apartment located close to the shops, bars and restaurants of Whitby's town centre and just a short walk to the beach. Sleeping up to 4 people this is the ideal retreat for couples or a small family.
  • 4 Guests
  • 2 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Private parking
  • Beach 0.5 miles
  • Pub 0.4 miles

Helmsley, North York Moors

Y055

(No dates selected)

£714 - £1545
per week
From £546 for a 3-night stay
  • 5 Star
  • An elegant and luxurious 3 bedroomed holiday cottage, ideally located in the charming North York Moors market town of Helmsley.
  • 6 Guests
  • 3 Bedrooms
  • 1 Pet
  • 3 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Open fire or woodburner
  • Beach 30 miles
  • Pub 0.1 miles

Whitby, Yorkshire Coast

W461

(No dates selected)

£1050 - £1578
per week
From £798 for a 3-night stay
  • 5 Star
  • Endeavour House is a beautifully presented town maintaining original features with luxury throughout. This property is centrally located within Whitby and would be an ideal location for a family holiday.
  • 8 Guests
  • 4 Bedrooms
  • 2 Pets
  • 3 Bathrooms
  • WiFi
  • Private parking
  • Parking permit provided
  • Pub 0.25 miles

Whitby, Yorkshire Coast

W452

(No dates selected)

£591 - £1217
per week
From £426 for a 3-night stay
  • 5 Star
  • This beautifully presented luxury holiday cottage sleeps upto 4 people. Only a short walk to Whitby town centre. The property benefits from a private parking space for two vehicles.
  • 4 Guests
  • 2 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Private parking
  • Beach 0.9 miles
  • Pub 0.3 miles

Kettlewell, Yorkshire Dales

DS257

(No dates selected)

£1117 - £2539
per week
From £848 for a 3-night stay
  • 4 Star Gold
  • Special offerBook and take a break between the 24th December - 3rd April and receive a 10% discount at this fantastic property! Plus pets go free and no booking fee call us on 01947 600700 to redeem this offer
  • 12 Guests
  • 5 Bedrooms
  • 4 Pets
  • 4 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Open fire or woodburner
  • Beach 46 miles
  • Pub 0.1 miles

Redcar, Yorkshire Coast

CL003

(No dates selected)

£312 - £563
per week
From £244 for a 3-night stay
  • 4 Star Gold
  • Delightful one bedroom pet friendly, Grade II listed cottage, restored and furnished to a very high standard whilst retaining many original features. Beamed ceiling, wood burning stove, wet room, private enclosed garden. Perfect for the romantics out there !
  • 2 Guests
  • 1 Bedroom
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • On-street parking
  • Parking permit provided
  • Open fire or woodburner
  • Beach 0.2 miles
  • Pub 0.2 miles

Whitby, Yorkshire Coast

W095

(No dates selected)

£401 - £746
per week
From £311 for a 3-night stay
  • 4 Star Gold
  • Delightful luxury modern apartment with patio and private parking near the centre of Whitby.
  • 4 Guests
  • 2 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 0.5 miles
  • Pub 0.3 miles
View more and filter search