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.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 22 self catering cottages in Sherborne to show you...
7 nights from £640 * booking fees included
Freshfields
57064 bedroom self catering cottage near Dorchester, Dorset.
Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...
7 nights from £640 *
From £64 per night + £38 booking fees
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
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £960 booking fees included
The Old Mill
45032 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.
If you are looking for a beautifully unique and special property for a perfect Dorset holiday, then look no further than The Old Mill. Formerly a working mill, this gorgeous proper...
7 nights from £960
7 nights from £603 booking fees included
Ivy Cottage
41222 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of a National Landscape, the cottage is situated ...
7 nights from £603
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £603 booking fees included
The Pump House
20981 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
Seize a unique opportunity and book a stay in this stunning converted pump house on the Somerset/Dorset border, close to the dramatic beaches and clifftop walks of the Jurassic Coa...
7 nights from £603
7 nights from £527 * booking fees included
Pippins
53602 bedroom, dog friendly character cottage near Beaminster, Somerset.
Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...
7 nights from £527 *
7 nights from £569 * booking fees included
The Old Coach House
13862 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...
7 nights from £569 *
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20% off
3 Jul 2026 - 10 Jul 2026
From £963.90 £834.12 booking fees included
7 nights from £1197 booking fees included
Beech Cottage
28875 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...
7 nights from £1197
7 nights from £399 booking fees included
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 £399
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20% off
29 Jun 2026 - 6 Jul 2026
From £638.00 £573.40 booking fees included
7 nights from £1491 booking fees included
Oak Tree House
61124 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
Oak Tree House is a particularly special property for gathering friends and family (plus the four-legged variety) together. Set in stunning grounds in the little village of Frampto...
7 nights from £1491
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20% off
4 Jul 2026 - 11 Jul 2026
£2713.00 £2233.40 booking fees included
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!
