Romantic Breaks on the Isle of Wight
Pick a luxury bolthole with a bubbling hot tub, or how about one with a pool? Maybe a luxury retreat with spectacular sea views or perhaps a secluded romantic cottage just right for two? The choices are endless for a romantic getaway on the Isle of Wight. Browse through our collection and take a step closer to the holiday of your dreams together. Read more
The Isle of Wight offers an idyllic base for a romantic adventure. Miles of coast path to explore, beaches peppered with fossils, amazing restaurants and eateries and lots of fun attractions to discover. And best of all? You can enjoy your break with the one you love most in a romantic cottage for two.
So you can share the holiday of a lifetime together, we have a selection of 136 available self-catering cottages primed and ready to welcome you. From choosing your cottage to opening the front door, we will guide you through every step so that the whole process is as smooth as possible. All of our cottages are handpicked; personally inspected and fully equipped to ensure your total comfort during your romantic break on the Isle of Wight.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
Search through 136 available romantic retreats on the Isle of Wight
7 nights from £648
2 St Josephs
35302 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
With sea views from the terrace and fresh, modern decor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect getaway for a small family, a couple or two ...
7 nights from £648
7 nights from £650
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...
7 nights from £650
7 nights from £651
1 Thatched Cottage
35082 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...
7 nights from £651
7 nights from £657
1 St Josephs
41832 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...
7 nights from £657
7 nights from £660
Lower Buoys
54572 bedroom luxury apartment near the beach in Seaview, Isle of Wight.
Looking for buried treasure and an Island adventure? Look no further than this superb ground floor, luxury apartment in a premier destination, in the heart of Seaview. Enjoy beachs...
7 nights from £660
7 nights from £695
Elm Cottage
35973 bedroom self catering apartment with sea views in Seaview, Isle of wight.
Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends travelling together, a couple or a family. From the front courtyard to ...
7 nights from £695
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £701
Apt 1 Springfield Court
35752 bedroom self catering apartment near the beach in Seaview.
Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...
7 nights from £701
7 nights from £709
Barton Manor Lake Cottage
35812 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...
7 nights from £709
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 *
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
