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.
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 206 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.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
Search through 206 available romantic retreats on the Isle of Wight
2 Sea Whispers
39783 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...
Price per week £405 - £950
Park Lodge Annexe
37202 bedroom, dog friendly holiday apartment near the beach in Shanklin.
Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...
Price per week £407 - £837
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.
September Cottage
36553 bedroom self catering cottage near the beach in Brook.
September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...
Price per week £413 - £898
Old Coastguards
36402 bedroom, dog friendly holiday cottage near the beach in Alum Bay, Isle of Wight.
Where to start in describing Old Coastguards? Our highlights are the tremendous views, log burning sauna with external heated shower, and roll-top bath, not to mention luxurious fu...
Price per week £460 - £1030
Chillerton Farm Barn
39643 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight
This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...
Price per week £495 - £1050
Bella Cottage
39033 bedroom self catering cottage in Newport, Isle of Wight
Located in the centre of the Island on the outskirts of the town of Newport, this is perfectly located to explore different places on the Isle of Wight. In the colder months, wrap ...
Price per week £495 - £1415
Manor Farm Cottage
41623 bedroom, dog friendly self catering cottage in Ventnor.
This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...
Price per week £500 - £1050
Westhill
41053 bedroom self catering apartment near the beach in Seaview, Isle of Wight
An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...
Price per week £550 - £1150
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
The Old Boat House
36763 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
The Old Boat House is an attractive period cottage set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This is a charming family home and can be rented...
Price per week £567 - £1240
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...
Price per week £612 - £1275