Cottages in Kent for the Summer Holidays
Spend your summer holiday in Kent and take advantage of the wonderful opportunities for walking and cycling through nature reserves and gorgeous woodland. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Choose from 8 school summer holiday cottages in Kent
7 nights from £706 booking fees included
Bloomsbury Cottage
61861 bedroom, dog friendly self catering cottage in Wadhurst.
For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...
7 nights from £706
7 nights from £1630 booking fees included
Dunks Cottage
60744 bedroom, dog friendly self catering cottage near Cranbrook.
Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...
7 nights from £1630
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 £1070 booking fees included
Strawberry Hole Barn
58142 bedroom thatched, dog friendly self catering cottage near Rye.
Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...
7 nights from £1070
7 nights from £744 booking fees included
Pump Cottage
57882 bedroom self-catering cottage in Rye.
Situated in the heart of Rye and just a short walk from the railway station, Pump Cottage is perfectly positioned for exploring this medieval town, 1066 country and the golden beac...
7 nights from £744
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £828 booking fees included
Hayesland Lodge
57001 bedroom, dog friendly self catering cottage near Rye.
This gem is situated in a peaceful and tranquil setting in a National Landscape (an Area of Outstanding Natural Beauty) with farmland views, a short drive from the coast and the me...
7 nights from £828
7 nights from £824 booking fees included
4 Church Square
55201 bedroom, dog friendly self catering cottage in Rye.
Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...
7 nights from £824
7 nights from £1198 booking fees included
Rose Cottage
53043 bedroom self catering cottage near the beach in Hythe.
Rose Cottage is an enchanting Grade II Listed period property situated in the heart of Hythe within walking distance of the Royal Military Canal, the seafront, and local amenities....
7 nights from £1198
7 nights from £909 booking fees included
Weald View Cottage
52842 bedroom self catering cottage near Maidstone.
Perfectly situated in the heart of the Kent countryside, this pretty semi-detached cottage with spectacular views across the Kent Weald is ideally located for walkers, couples and ...
7 nights from £909
At Classic Cottages we understand how important your accommodation is in making or breaking your holiday experience. That's why we handpick all of our properties, personally inspecting each one so that exacting standards are met. From start to finish we want your holiday to be as easy and relaxed as possible, and will provide you with help and support every step of the way. All you need to do? Pick your favourite cottage and embrace the holiday of a lifetime in Kent.
