We have 22 self catering cottages available to rent in May in North Yorkshire
7 nights from £751
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 £751
7 nights from £538
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 £538
7 nights from £735
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 £735
7 nights from £680 *
Greystones
57375 bedroom dog friendly self catering cottage near the beach in Staithes.
Welcome to Greystones, a fantastic holiday property for all the family, full of original features and perfectly located in the beautiful seaside village of Staithes in North Yorksh...
7 nights from £680 *
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £663
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 £663
7 nights from £683
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 £683
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
7 nights from £735
Hillrise
55074 bedroom self catering cottage near Whitby.
In the picturesque Yorkshire Moors village of Glaisdale, close to the beautiful east coast, Hillrise is a delightful cottage to while away your holiday in. You will be charmed ...
7 nights from £735
From £99 per night
Sammi's Freight Train
5287Dog friendly vintage railway carriage with wood-fired hot tub near Richmond.
Immerse yourself in a restful rural getaway and escape the rush of everyday life. Disappear into the heart of the Yorkshire Dales and return for evening starlit soaks in the wood-f...
From £99 per night
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10% off
19 Dec 2025 - 24 Dec 2025
From £129.60 £116.64 per night
7 nights from £605
The Dairy
51881 bedroom self catering cottage near Settle.
The Dairy is a charming, newly renovated cottage, perfectly placed within the Yorkshire Dales yet close to the Forest of Bowland and the delights of the Lake District. Situated amo...
7 nights from £605
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
