Holiday Cottages Sleeping 5 People in Dorset
Bundle up your favourite people and get on your way to Dorset. We have a selection of 19 self-catering cottages sleeping up to 5 people available. Invite four of your friends or family, or simply make use of the extra space, our cottages that sleep 5 combine home-comforts with modern luxuries. Don't miss out on your favourite and book your luxury self-catering cottage now. Read more
Take a winter break in a rural retreat to put a fun twist on traditional celebrations, and then get planning for summer and enjoy a quintessential seaside holiday. Whether you choose a short break or a whole month of exploration and relaxation, Dorset provides an idyllic playground. From its stunning Jurassic coastline to its beautiful rolling countryside to its pretty medley of towns and villages, take your pick of activities for the day and then return to your own private accommodation.
If you have got friends who you haven't seen for a while or are looking for an excuse to get the family together for some quality time, our self-catering cottages sleeping 5 people offer ample space and comfort. With real beds for everyone to snuggle into, we make sure everything you could need and more is available and no one gets cut short without a mug to drink from or somewhere comfy to settle into. You'll even find there are enough teaspoons for everyone.
Dorset Cottages that Sleep 5 People
At Classic Cottages we want your holiday experience to be the best it can be for you and everyone in your party. That's why all of our cottages are handpicked; personally inspected and fully equipped for your total ease and comfort. We are always on hand to offer support, and will help you every step of the way towards the holiday of your dreams. Many of our cottages are dog-friendly too, meaning everyone can enjoy a holiday in Dorset.
Find your favourite Dorset cottage for 5 from our 19 available retreats
7 nights from £436
Meadowbank
26443 bedroom holiday cottage near Bridport, Dorset.
If you are looking for a peaceful, rural setting to spend your well deserved holiday, then look no further. This sunny south-facing cottage is sat perfectly on the edge of the beau...
7 nights from £436
7 nights from £465
The Parlour
26622 bedroom, rural cottage near the beach near Bridport, Dorset.
The Parlour is an excellent choice for a family, with French doors opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three single...
7 nights from £465
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 £561
Hatts Barn
20932 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Hatts Farm is a working farm located in an Area of Outstanding Natural Beauty. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire bord...
7 nights from £561
7 nights from £604
Halcyon Cottage
46933 bedroom holiday cottage near the beach in West Lulworth, 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
7 nights from £584
Sturthill Stable
28293 bedroom, dog friendly self catering cottage 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 £584
7 nights from £595
Barn Owls Cottage
30153 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...
7 nights from £595
7 nights from £643
2 Penny’s Cottages
25313 bedroom holiday cottage in Corfe Castle, Dorset.
Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...
7 nights from £643
7 nights from £686
Sunnyholme
14604 bedroom holiday cottage near the beach in Studland, Dorset.
The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme is an extrem...
7 nights from £686
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
7 nights from £707
Meadows Barn
42933 bedroom self catering cottage near Yeovil, Dorset.
Meadows Barn is on the edge of the tranquil Dorset village of Halstock, with far reaching views over the surrounding countryside, ideal for a family holiday or a great base for fri...
7 nights from £707
7 nights from £767
Sandy Days
32153 bedroom, dog friendly cottage near the beach in Christchurch.
Avon beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this recently renovated holiday bolthole. The cool shades of blue and the pl...
7 nights from £767