Holiday cottages with a pool
Escape and have a dip in your holiday cottage swimming pool. Float away your worries and relax in style. Choose a large holiday home with a swimming pool for that long-awaited summer holiday so the little ones (and bigger ones!) always have something to do and happy family memories can be made. Or pick a bijou cottage with a private pool so you and your loved one can make like a pair of otters and float hand in hand for total relaxation. Read more Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.
63 luxury self catering cottages with pools to rent
7 nights from £659
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 £659
7 nights from £1500
Chestnut Retreat
57502 bedroom self catering apartment with swimming pool in Ossett
Visit West Yorkshire and relax in this luxury apartment with an onsite spa. After a day of visiting local attractions or walking in the hills, return to spend some quality time in ...
7 nights from £1500
From £110 per night
Farm Cottage
57182 bedroom, dog friendly cottage near Ventnor.
For those looking for a peaceful and calming cottage then look no further than Farm Cottage, it's set in the delightful grounds of the owners' home and has been furnished with care...
From £110 per night
From £72 per night
The Stables
56511 bedroom, dog friendly holiday cottage close to the beach, near Ventnor.
Welcome to The Stables, a romantic getaway for two! Close to the seaside town of Ventnor, with its beautiful beachfront, you can explore this corner of the Island and then retreat ...
From £72 per night
7 nights from £869
65 Lower Maen Cottage
55973 bedroom cottage with sea views near Falmouth, South Cornwall.
Welcome to this lovely, light-filled holiday home with delightful sea views, situated just a short stroll away from a pretty, sandy cove and the harbourside town of Falmouth. Set i...
7 nights from £869
From £85 per night
Sunrise and Stars
5672Dog friendly shepherds hut with a hot tub near Ventnor.
Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...
From £85 per night
7 nights from £2596
Lamellen House
55817 bedroom, dog friendly holiday home near Wadebridge, North Cornwall.
Come and enjoy a country break like no other, at the glorious quintessential Cornish estate of Lamellen. Wend your way up the drive, passing the beautiful show of camellias, magnol...
7 nights from £2596
7 nights from £617 *
Driftwood
5613A dog friendly luxury retreat with private hot tub sleeping 4.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...
7 nights from £617 *
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Colwell Bay Cottages
7 nights from £1234
7 nights from £617 *
Escape Away
5612A luxury retreat with private hot tub and use of swimming pool.
New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...
7 nights from £617 *
Whether you're having fun with the whole family, children splashing and games with inflatables, or relaxing on your lilo as your other half sits on the side patiently holding your glass of fizz, complete your holiday with a holiday cottage with a swimming pool.
Browse through our collection to find holiday homes with a private pool and luxury cottages with a pool in the UK. Relax in the knowledge that you'll have something to do come rain or shine just on the doorstep of where you're staying. Our self catering cottages with a private pool are the perfect way to treat yourself to a luxury holiday.
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