Romantic Hideaways for Two in Dorset
Looking forward to spending some quality time with your partner away from the distractions of everyday life? Book a romantic break in Dorset, turn off your phone and give your beloved your undivided attention in your own private paradise. A romantic retreat will refresh your relationship and leave you with lots of happy memories. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.50 luxury cottages for couples in Dorset
7 nights from £363
Spring View Cottage
57831 bedroom cottage with countryside views near Dorchester, Dorset.
A sweet bolthole for two, Spring View Cottage is nestled in the beautiful Dorset countryside. Easily accessible but far enough away to feel like you have really escaped, this compa...
7 nights from £363
7 nights from £373
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 £373
Choose our flexible booking option and have the ability to cancel anytime.
7 nights from £377
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 £377
7 nights from £383 *
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 £383 *
7 nights from £400
The Dairy
26631 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French doors to its own enclosed outside space – the...
7 nights from £400
7 nights from £412 *
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 £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 £415 *
Sturthill Stable
28293 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
This beautiful barn conversion at the heart of a working farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the family ...
7 nights from £415 *
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £419
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 £419
7 nights from £478 *
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 £478 *
Whether you are looking forward to starting off the New Year in style, taking a well-deserved summer break or fancy a cosy winter retreat together, the choices are endless for a romantic break together in Dorset. Browse through our selection of luxury self-catering cottages perfect for a couple's getaway. You may pick an old favourite or find a new place to be; whichever you choose you're guaranteed total comfort during your stay.
At Classic Cottages, we take quality accommodation seriously. Knowing the difference your accommodation can make to your experience, we pride ourselves on marketing only the finest self-catering cottages in Dorset. All of our cottages are handpicked; regularly checked and fully equipped, right down to the last teaspoon.
