Holiday Cottages Sleeping 5 People in Dorset

Bundle up your favourite people and get on your way to Dorset. We have a selection of 30 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. 

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 30 available retreats

4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.

Escape to the coast and this fabulous cottage where you can watch the seascape change all day long. Just minutes from the harbour at Lyme Regis and its iconic Cobb, this Grade II L...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £850 - £2377

6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.

Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £1037 - £2850 *

* Includes 30% off for parties up to 8 + 2 cots between 1 Sep and 15 Dec 2018. Bedroom 1 and the single bed in Bedroom 3 are excluded at this rate

4 bedroom, dog friendly holiday cottage near Beaminster, Dorset.

This tranquil and elegant period farmhouse has a luxurious contemporary interior, spacious flexible accommodation and a beautiful enclosed garden. The glorious west Dorset location...

  • Sleeps 8
  • Dogs welcome
  • Changeover Fri

Price per week £1158 - £2185

25% off for parties up to 4 between 1 Sep and 29 Sep 2018. Bedrooms 3 and 4 are excluded at the discounted rate.

5 bedroom, dog friendly self catering cottage near Bridport, Dorset.

This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £692 - £1989

Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 6 in 2 properties
  • Changeover Fri

Price per week £778 - £1766

Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

Price per week £826 - £1871

We’re here to help you find your perfect place to stay 7 days a week.

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 beds...

  • Sleeps 9 + 2 cots in 2 properties
  • Changeover Fri

Price per week £868 - £2092

The Linhay is a tucked away single-storey retreat – an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel court...

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

Price per week £1048 - £2199

With stunning rural views from your deck, and a fabulous open plan interior, Furrow Lodge snuggles into the hillside in the delightful Dorset countryside and offers a real opportun...

  • Sleeps 13 + 3 cots in 3 properties
  • Changeover Fri

Price per week £1374 - £2988

Enjoy a holiday with a difference, relax under canvas and soak up the peace and tranquility of the rolling Dorset countryside, with luxury en suite facilities, glamping style. Blac...

  • Sleeps 16 + 3 cots in 3 properties
  • Changeover Fri

Price per week £1503 - £3535