Holiday Cottages for 5 People
Gather your family or herd up your friends, a holiday in a luxury self-catering cottage for 5 people awaits. Providing the perfect base for adventure in the day and offering total comfort for long afternoons and evenings relaxing together, our cottages combine home-comforts with modern luxuries. Secure your favourite now and get ready to make memories to last a lifetime. Read more
There's no better time to secure your dream holiday cottage than the present. Cosy winter breaks help vanquish the winter blues and summer getaways provide the subject for photo albums packed with happy memories. Out of season holidays are great for both short breaks and longer holidays, providing tranquillity away from busier times. Book a spontaneous short break and then pencil in a longer holiday to look forward to. With so many beautiful places to visit and luxury cottages to choose from, you'll be spoilt for choice.
Whether you're looking for a rural retreat in the heart of lush countryside, a seaside bolthole with stunning ocean views, or a town hub combining home-comforts with great access to local amenities, we'll help you find a holiday cottage that ticks all the boxes. From quaint thatched cottages to clifftop nests, our self-catering properties are diverse in nature and consistent in quality.
Holiday Cottages for 5 People
At Classic Cottages, we pride ourselves on marketing only the highest quality cottages. Understanding the importance of accommodation in making or breaking your holiday, we ensure only the best cottages are on our books. Regularly inspected and fully equipped with everything you could need and more, holidays with Classic Cottages takes the stress out of your whole experience.
We have 707 cottages that sleep 5 people
7 nights from £842
Keepers Cottage
40704 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...
7 nights from £842
7 nights from £849
Carngowil Farmhouse
55634 bedroom, dog friendly self catering cottage near Fishguard.
Nestling in a spectacular corner of Pembrokeshire this splendid Welsh retreat, dating back to the 14th Century, offers delightful tradition with stylish modern comforts. Carngowil ...
7 nights from £849
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 £858
Lower St Winnolls
45104 bedroom, dog friendly cottage with sea views near Looe, Cornwall.
Lower St Winnolls is a true Cornish gem dating back 250 years whilst benefiting from all the modern conveniences of 20th Century living including an electric car charging point and...
7 nights from £858
7 nights from £880
The Granary
29824 bedroom, rural holiday cottage in Widemouth Bay, North Cornwall.
Close to the shores of Widemouth Bay on the north Cornish coast this luxurious, semi-detached farmhouse with enclosed garden and hot tub will provide the perfect holiday for you al...
7 nights from £880
7 nights from £881
Freshfields
57064 bedroom secluded cottage with large grounds near Dorchester, Dorset.
Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...
7 nights from £881
7 nights from £908
Inglefield
5637Dog friendly holiday cottage with 4 bedroom near the beach in St Helens.
This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...
7 nights from £908
7 nights from £948
Antigua
31124 bedroom dog friendly cottage with sea views in Portscatho, South Cornwall.
This lovely, extremely comfortable and stylish end of terrace property enjoys amazing sea views of Gerrans Bay. Its terraced rear garden – a plantsman's delight – has relaxing shel...
7 nights from £948
7 nights from £949
Stable Tallet
17194 bedroom, holiday cottage near Colyton, South Devon with a hot tub
Stable Tallet is in an Area of Outstanding Natural Beauty close to east Devon’s stunning Jurassic Coast. Set on a friendly working farm, this detached home-from-home has the bonus ...
7 nights from £949
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 £999
Quay House
53723 bedroom self catering cottage with sea views in Fishguard.
Just over a mile from some of Pembrokeshire's most glorious beaches, soak up the enchanting estuary, sea and mountain views from spectacular Quay House, a fabulously renovated, sem...
7 nights from £999
7 nights from £1008
South Barn at Pickeridge
52113 bedroom, dog friendly self catering cottage near Haywards Heath.
South Barn at Pickeridge is tucked away on a 120 acre working farm in a secluded valley between West Hoathly and Ardingly. It's the perfect retreat for families and friends looking...
7 nights from £1008
