May half term holiday cottages
With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover a beautiful corner of the UK. Read more Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.
We've got 16 holiday cottages matching your search in North Yorkshire...
7 nights from £1200
The Old Farmhouse
57923 bedroom, dog friendly self catering cottage in Pickering.
Nestled on the edge of the North York Moors in the charming town of Pickering, this Grade II Listed terraced cottage effortlessly combines historic charm with contemporary luxury. ...
7 nights from £1200
7 nights from £553
Fell View
58123 bedroom, dog friendly self catering cottage near Hawes.
If you want to get away from it all, why not visit Fell View in Gunnerside! A cosy three bedroom cottage in the heart of the village with a local pub on your doorstep and a front c...
7 nights from £553
7 nights from £612
Joe House
57792 bedroom self catering cottage near Hawes.
Once inside you will be enveloped in the essence of a Yorkshire country cottage with beams, hand hewn staircase, walls which have been carefully renovated to ensure the traditiona...
7 nights from £612
7 nights from £781
Nettlebed
57683 bedroom, dog friendly self catering cottage near Hawes.
Come away to Yorkshire and experience the authentic, rustic charm of an original Yorkshire stone cottage. Nettlebed is nestled on the hillside with amazing views over Swaledale and...
7 nights from £781
7 nights from £587
The Old Stable
5790A cosy 2 bedroom, dog friendly self catering cottage near Hawes.
The Old Stable nestles in a splendid, elevated position with far reaching views of the hills and dales in the hamlet of Crackpot in the heart of the Yorkshire Dales. A delightfully...
7 nights from £587
7 nights from £638
The Haven
57782 bedroom self catering cottage near Hawes.
As its name implies, The Haven is a lovely stone cottage in the heart of the Yorkshire Dales in the quintessential country village of Gunnerside with its pretty bridge, picturesque...
7 nights from £638
7 nights from £756
School House
57043 bedroom, dog friendly self catering cottage near the sea in Muston near Filey.
This charming gem of a cottage is located in the pretty village of Muston, Yorkshire, which is listed in the Domesday Book. Close to the seaside town of Filey and one of England's ...
7 nights from £756
7 nights from £518 *
Sealark
56262 bedroom, dog friendly holiday cottage near the beach in Staithes.
Close to the beautiful coastline, cliffs and sandy beaches of Runswick Bay, Staithes and Whitby sits this gem of a cottage sleeping four. Exuding a subtle and stylish coastal charm...
7 nights from £518 *
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £744
Briar Lea
56942 bedroom, dog friendly cottage with sea views in Robin Hoods Bay.
Nestled in the quiet coastal village of Fylingthorpe with views across the sea to the rugged Yorkshire coastline and within minutes of the historic Robin Hood's Bay, this beautiful...
7 nights from £744
7 nights from £880
Ivy House
56114 bedroom, dog friendly self catering cottage near Thirsk.
Nestled in the picturesque Yorkshire village of Borrowby, Ivy House is a beautifully renovated farmhouse steeped in history and with bags of character which gives a nod to its hist...
7 nights from £880
With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to North Yorkshire. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.
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