Isle of Wight holiday cottages
Our exclusive collection of cottages on the Isle of Wight have been handpicked and inspected by our team of island experts. Home to some of the best coast and countryside in Britain, the Isle of Wight is perfect for a romantic break for two or a family gathering with dogs and all. For a sneak peek of what awaits you on the island, check out our new <webcams in Ryde and Freshwater.
132 cottages
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Sleeps 12 dogs allowed
St Andrews
1.1 miles SW of Yarmouth
From £2727 a week
Wow! This spectacular converted church has the makings for the most amazing holiday, set in an elevated position with panoramic views across the surrounding countryside and a glimpse of the sea. The l...
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Sleeps 2 dogs allowed
The Stables
3.2 miles W of Ventnor
From £72 a week
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 back to your private...
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Sleeps 4 dogs allowed
Farm Cottage
3.2 miles W of Ventnor
From £110 a week
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 and attention to de...
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Sleeps 2 dogs allowed
Sunrise and Stars
3.3 miles W of Ventnor
From £85 a week
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 captivating countryside a...
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Sleeps 4 dogs allowed
Driftwood
Freshwater
From £617 a week
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 love to explore as muc...
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Sleeps 4 dogs allowed
Escape Away
Freshwater
From £617 a week
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 yourself for a peaceful...
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Sleeps 8 dogs allowed
House of Logs
Totland
From £665 a week
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and dog friendly, the hous...
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Sleeps 5
Stargazers' Retreat
3.6 miles W of Ventnor
From £149 a week
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated just outside the pre...
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Sleeps 4
Lazydays Hideaway
3.6 miles W of Ventnor
From £145 a week
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 want to escape from a b...
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Sleeps 6 dogs allowed
The Shute
1.8 miles W of Ventnor
From £864 a week
This gorgeous cottage, set in the breathtaking location of St Lawrence, has a large patio and unrivalled sea views. A truly magical place to sit and enjoy the scenery, the seaward facing conservatory ...