South Wight Cottages
We've got 31 holiday cottages in South Wight. South Wight is the epitome of the classic seaside holiday. With golden sands, the promenade and even Sandown pier to explore, there’s plenty to keep you busy whilst visiting the south of the Isle of Wight. The coastal path is a walker’s paradise and the numbered bridleways make it really easy for horse riders to get around the isle.Read more
With an amazing view around every corner, it’s really worth getting out and about to see all that the island has to offer. There’s a reason the Victorians loved the Isle of Wight and South Wight was the main haven for these visitors. Sandown, Shanklin and Ventnor were especially popular and still remain so today.
Enjoy a walk along the promenade next to the beaches or head further inland to visit the quaint ‘chocolate box village’ of Godshill for a classic cream tea. St Catherine’s point, the most southern part of the island, is a lovely day out as there are plenty of walks and you can head into the lighthouse for a tour around.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 31 self catering cottages in South Wight to show you...
7 nights from £508
Oakham Cottage
35162 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight
Oakham Cottage can be found in the heart of the Isle of Wight, surrounded by rolling countryside and the perfect location for exploring all treasures this lovely Island has to offe...
7 nights from £508
7 nights from £508
Grafton Cottage
35012 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.
Located in a tranquil rural setting and part of Bagwich House, this sympathetic barn conversion is set over two floors and is one of three holiday properties. A short drive from th...
7 nights from £508
Bagwich House
7 nights from £1524
7 nights from £1146
The New House
40254 bedroom self catering cottage in Godshill, Isle of Wight
Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...
7 nights from £1146
7 nights from £508
Blakesley Cottage
55652 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...
7 nights from £508
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
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 £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
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 £525
Grace Cottage
42091 bedroom, dog friendly holiday cottage close to the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...
7 nights from £525
7 nights from £864
The Shute
43993 bedroom dog-friendly self catering cottage with sea views near Ventnor, Isle of Wight.
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 ...
7 nights from £864
