Cottages For May in The Cotswolds
Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit The Cotswolds Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 10 self catering cottages available to rent in May in The Cotswolds
7 nights from £690 *
The Gatehouse
60332 bedroom self catering cottage in Malmesbury.
If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...
7 nights from £690 *
7 nights from £896
2 Old Turnpike Cottages
58662 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.
Sitting in the picturesque village of Middle Barton, just a short drive from Chipping Norton and the exclusive Soho Farmhouse, Diddly Squat Farm and The Farmers Dog pub, lies this ...
7 nights from £896
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10% off
9 May 2026 - 17 May 2026
From £996.00 £896.40
7 nights from £1367
The Yew Trees
58622 bedroom dog friendly self catering cottage near Cheltenham.
This charming holiday cottage, nestled in the peaceful countryside just outside Cheltenham and the gorgeous Cotswolds, offers the perfect retreat for a tranquil getaway. Set in a r...
7 nights from £1367
7 nights from £625
Oak Tree Cottage
57412 bedroom self catering cottage near Burford.
Oak Tree Cottage is a delightful semi-detached barn conversion and is nestled next to its neighbour, The Gallery (5756). They can be booked together for larger gatherings. The acco...
7 nights from £625
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From £950 per night
King John's Palace
57306 bedroom self catering home near Burford
Stay in style at King John's Palace, where kings and queens resided before you. A beautiful historic home close to the quintessential Cotswold town of Burford. This unique hidden g...
From £950 per night
Weighbridge Barn
7 nights from £1388
7 nights from £694
Weighbridge End
56471 bedroom, dog friendly self catering cottage near Chippenham.
This stunning barn located on the edge of the Cotswolds is a gem of a property just waiting to be discovered. Sympathetically converted with nods to its previous life as a working ...
7 nights from £694
7 nights from £694
Stable End
56481 bedroom, dog friendly self catering cottage near Chippenham.
Located in Grittleton, a short drive from both Chippenham and Bath, just on the edge of the Cotswolds, an area of beautiful countryside and picturesque villages, come and discover ...
7 nights from £694
7 nights from £647
The Farthings
56772 bedroom self catering cottage near Moreton-In-Marsh
If you are looking for a cosy Cotswold bolthole to escape to, then The Farthings won't disappoint. This pretty terraced cottage sits pretty amongst its neighbours and is nestled ju...
7 nights from £647
7 nights from £755
The Apartment, Broadway
54561 bedroom self catering apartment in the heart of Broadway.
If you are looking for the perfect pad to explore the Cotswolds, then The Apartment, Broadway couldn't offer a more convenient location. Beautifully presented throughout, the apart...
7 nights from £755
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!
Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in The Cotswolds . So have a look through our 10 holiday cottages available this May in The Cotswolds .
