Cottages in Dorset for May Day Bank Holiday
Escape from the rhythm of everyday life and kick start your summer. Across Dorset, colours and new life pervade the landscape and lots of events and festivities take place. Choose a luxury cottage from which to enjoy Dorset this May Day bank holiday and spend your break in a home-from-home. All of our cottages have been personally inspected and handpicked. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Pick from 48 cottages for May Day bank holiday
7 nights from £320
The Dairy
26631 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
The Dairy is an extremely comfortable single-storey cottage in this small and friendly farm development. The property has French doors to its own enclosed outside space – the patio...
7 nights from £320
7 nights from £320
The Linhay
26611 bedroom cottage near the beach near Bridport, Dorset.
The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...
7 nights from £320
7 nights from £336
Kingfishers
60351 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...
7 nights from £336
7 nights from £405
Fox Cottage
47121 bedroom stylish cottage in Beaminster, Dorset.
Tucked away in an oh-so-pretty part of historic Beaminster, Fox Cottage is a gorgeous retreat for two. As soon as you arrive at this picture-perfect terraced cottage, you will want...
7 nights from £405
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7 nights from £412
Loaf At The Granary
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
**Loaf At The Granary can accommodate flexible check in days – please contact us to request.** Loaf At The Granary is a gorgeous and sympathetic restoration of an ancient Dorset...
7 nights from £412
7 nights from £412
Swallows' Rest
46441 bedroom, dog friendly cottage near Beaminster, Dorset.
The sleepy west Dorset countryside awaits you at this cute bolthole for two (plus your four-legged friends). Tucked away at the end of the owners' garden, this converted barn is hi...
7 nights from £412
7 nights from £431 *
The Granary
56832 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
Tucked away in a rural corner of west Dorset you will find The Granary; a single-storey cottage with a shared two acre woodland and wildflower meadow to while away holiday days in....
7 nights from £431 *
7 nights from £431 *
The Dairy
56822 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...
7 nights from £431 *
From £64 per night
La Cabine Francaise
47261 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.
Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...
From £64 per night
7 nights from £453
Badgers Cottage
30141 bedroom, dog friendly cottage near Bridport, Dorset.
This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty (now known as National Landscapes) on West Hembury Farm. Badgers Cottage is an ...
7 nights from £453
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
Planning on a solo escape this May Day to relax and revive? How about a romantic retreat in a cosy cottage for two? Perhaps you'd like to enjoy a family break and spend some quality time together in a spacious retreat? From country to coast, we have a range of luxury self-catering cottages in Dorset, primed and ready to welcome you. Many are dog-friendly too, so no one gets left behind. Choose from our 48 available properties and get ready to spend a May Day bank holiday to remember. At Classic Cottages, we understand what makes holidays fantastic and pride ourselves on marketing the finest self-catering accommodation around. With each holiday cottage regularly inspected and fully equipped, everything you could need and more for your stay is supplied. Book with confidence with Classic Cottages.
