Sherborne Cottages
A fabulous castle built by Sir Walter Raleigh, so well preserved it remains a family home to this day, an impressive abbey and any number of medieval buildings – it's no wonder that Sherborne is a favourite among historians. Sherborne's glory isn't all in the past, though – this gorgeous town was recently voted the best place to live in the South West by The Times, and has some of the most diverse shopping you'll find anywhere.
We have 34 self catering cottages in Sherborne to show you...
7 nights from £503
The Gardens
54062 bedroom, dog friendly cottage in historic Sherborne, Dorset.
From the rolling hills of the Dorset countryside to the beautiful historic streets of Sherborne and down to the Jurassic Coast, explore it all whilst staying at The Gardens. This c...
7 nights from £503
7 nights from £366
Owl's Nest Cottage
29421 bedroom, dog friendly cottage near Sherborne, Dorset.
This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...
7 nights from £366
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.
7 nights from £497
Pound Farm Cottage
40761 bedroom thatched cottage near Sherborne, Dorset.
Pound Farm Cottage is a hidden gem; this Listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...
7 nights from £497
7 nights from £453
Poacher's Cottage
45222 bedroom cottage with outside pool near Dorchester, Dorset.
Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...
7 nights from £453
7 nights from £453
Gamekeeper's Cottage
45232 bedroom cottage with outside pool near Dorchester, Dorset.
Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...
7 nights from £453
7 nights from £453
Woodcutter's Cottage
45242 bedroom cottage with outside pool near Dorchester, Dorset.
Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...
7 nights from £453
7 nights from £659 *
Gardener's Cottage
45253 bedroom cottage with outside pool near Dorchester, Dorset.
A stay at Gardener's Cottage brings you everything you could wish for in a holiday location - spacious rooms, beautiful furnishings and a stunning setting complete with outdoor hea...
7 nights from £659 *
Dominey's Yard
7 nights from £2018
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!
7 nights from £769
Keepers Cottage
51943 bedroom, dog friendly cottage with wonderful views near Yeovil, Somerset.
Keepers Cottage is the former gamekeeper's cottage for Montacute House and is set in the rolling countryside of South Somerset, close to the historic village of Montacute. Stunning...
7 nights from £769
From £140 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 £140 per night