Weymouth Cottages
A town of two halves - the old town forms a cluster of quirky mismatched cottages around the harbour, while the new town is an elegant parade of Georgian town houses on the seafront.
We have 17 self catering cottages in Weymouth to show you...
7 nights from £570
No 1 By The Sea
49652 bedroom holiday apartment near the beach near Weymouth, Dorset.
Just a short stroll from the sea, this super-stylish apartment is a gorgeous retreat with an added touch of luxury. Situated on the ground floor of a smart, modern apartment buildi...
7 nights from £570
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10% off
21 May 2022 - 28 May 2022
£731.60 £658.80
7 nights from £604
Halcyon Cottage
46932 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.
Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...
7 nights from £604
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £344
The Stables
19651 bedroom, rural holiday cottage near the county town of Dorchester, Dorset.
This quaint cottage is set within the rural hamlet of Pallington. The Stables is a self-contained, single storey cottage with a welcoming open plan design. The entrance hall leads ...
7 nights from £344
7 nights from £425
Beehive Cottage
40732 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Beehive Cottage is a charming and cosy cottage on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the ...
7 nights from £425
7 nights from £562
Rectory Cottage
47952 bedroom cottage near Bridport, Dorset
Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. From the moment you pull in to the driveway you will lov...
7 nights from £562
7 nights from £688
Park Farm Byre
49563 bedroom, dog friendly holiday cottage with hot tub near Dorchester, Dorset.
Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with wood-fired hot tub. All on one level (apart from two steps from the sitting-room to t...
7 nights from £688
7 nights from £526
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £526
7 nights from £516 *
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 dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...
7 nights from £516 *
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 £619
Barn Owls Cottage
30153 bedroom, dog friendly cottage near Bridport, Dorset.
Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...
7 nights from £619
West Hembury Farm
7 nights from £977
