Holiday Cottages Sleeping 5 People in Dorset
Bundle up your favourite people and get on your way to Dorset. We have a selection of 23 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 23 available retreats
7 nights from £419
Meadowbank
26443 bedroom holiday cottage near Bridport, Dorset.
This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...
7 nights from £419
7 nights from £442
The Parlour
26622 bedroom, rural cottage near the beach near Bridport, Dorset.
The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...
7 nights from £442
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10% off
18 May 2019 - 25 May 2019
£582.13 £523.80
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 £488
Hatts Barn
20932 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family-room (the twin...
7 nights from £488
7 nights from £493
Northgate
32013 bedroom self catering cottage in Wareham, Dorset.
Wareham is the gateway to the Jurassic Coast, a fabulous base from which to explore the Isle of Purbeck. Just within the ancient Saxon walls of this historic market town, Northgate...
7 nights from £493
7 nights from £546
Old Down Cottage
19343 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
This is an excellent base for exploring rural and coastal Dorset. Cranborne Chase (an Area of Outstanding Natural Beauty) is on the doorstep, and the beaches of the Jurassic Coast ...
7 nights from £546
7 nights from £548
Brook Cottage
11283 bedroom holiday cottage in Corfe Castle, Dorset.
Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...
7 nights from £548
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30% off
27 Apr 2019 - 4 May 2019
£782.41 £547.40
7 nights from £554
Meadows Barn
42933 bedroom self catering cottage in rural 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 £554
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20% off
19 Apr 2019 - 26 Apr 2019
£692.03 £553.60
7 nights from £558
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 £558
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 £561
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 £561
7 nights from £592
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 £592