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 15 holiday cottages matching your search in Yorkshire...
7 nights from £762
No 9
60522 bedroom, dog friendly self catering cottage near York.
Tucked away in a quiet gated community only steps from the pretty centre of the market town of Helmsley, sits No 9, a pretty two-storey cottage surrounded by beech hedging and with...
7 nights from £762
7 nights from £755
Number 5
58683 bedroom, dog friendly holiday cottage near the beach in Filey.
This delightful holiday cottage in Filey offers a perfect blend of coastal charm and countryside accessibility as it's just a short stroll from the seaside but has easy access to t...
7 nights from £755
7 nights from £648
Yore View
59582 bedroom, dog friendly self catering cottage near Hawes.
A warm welcome awaits at Yore View in the Yorkshire Dales, perched on a ridge with amazing views over the countryside and surrounded by a large garden, this thoughtful renovation h...
7 nights from £648
From £99 per night
Albie's Freight Train
5967Dog friendly vintage railway carriage with a wood-fired hot tub near Richmond.
All aboard this little beauty, a stunning converted train carriage complete with wood-fired hot tub. It's the perfect romantic, dog friendly getaway for two with gorgeous countrysi...
From £99 per night
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 £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 £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 £723
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 £723
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
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
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50% off
29 Dec 2025 - 5 Jan 2026
£787.00 £393.50
7 nights from £782
The Old Post Office
57053 bedroom, dog friendly self catering cottage near York.
Nestled in the picturesque village of Helperby near Thirsk, set in the Howardian Hills, this charming three bedroom dog-friendly cottage with hot tub, which was once the old Post O...
7 nights from £782
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 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.
