Two night breaks in Isle of Wight
A weekend away or two night short break in Isle of Wight is so simple. No major preparations or need to pack up your life, just the perfect excuse to get away from it all for your favourite holiday cottage and slip under the radar of everyday life. With hand picked cottages across the UK, there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...
We have 48 holiday cottages available in Isle of Wight for a two night break
The Old Dairy
7 nights from £1022
7 nights from £372
The Studio
57531 bedroom, dog friendly,cosy cottage near Ryde.
Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...
7 nights from £372
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 £716 *
Tangle Cottage
56694 bedroom family home close to the beach in Seaview.
Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...
7 nights from £716 *
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 £650
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £650
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 *
Colwell Bay Cottages
7 nights from £1234
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
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 *
From £145 per night
Lazydays Hideaway
53811 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...
From £145 per night
