Ventnor Cottages
Home to the thriving Isle of Wight arts scene and the beautiful botanical gardens, Ventnor offers up a plethora of activities for island visitors. Sheltered by St Boniface Downs, the town has its own microclimate meaning it remains particularly warm throughout the year. Make the most of the climate and take a trip to the botanical gardens, originally a Victorian lung hospital where patients were sent to recover in the clean air of the island. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 23 self catering cottages in Ventnor to show you...
7 nights from £1035
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1035
7 nights from £706
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £706
7 nights from £888
St Albans House
39804 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...
7 nights from £888
7 nights from £801
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £801
7 nights from £650
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 £650
7 nights from £427 *
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...
7 nights from £427 *
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20% off
4 Apr 2025 - 11 Apr 2025
From £731.00 £584.80
7 nights from £564 *
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 £564 *
7 nights from £707 *
Sheldonia
51093 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...
7 nights from £707 *
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 £861
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
This superb two-storey, first floor apartment dating back to 1863 is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the use of a la...
7 nights from £861
7 nights from £493
Westhill View
48822 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.
With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...
7 nights from £493
Ventnor also (supposedly) benefits from having the most daylight hours in the UK, another perk to visiting in the summer. With the extra daylight hours, get stuck in with local artists and musicians at the Ventnor Exchange or book tickets for the Ventnor Fringe festival in August.
Ventor’s sea front, also known as Ventnor Haven, is an amazing spot for fishing. There’s a wonderful fishery on the front where you can find a fresh catch to take home for dinner. Most of the crab served on the island is from Ventnor too so you’ll be sure to find some fresh seafood dishes served in the local restaurants and bistros of this area.
Ventnor is at the south of the isle, just east from St Catherine’s point and Niton. To the east of Ventnor you’ll find the small village of Bonchurch which has a big literary claim to fame. The village has played host to many famous authors, including Charles Dickens and the poet Algernon Charles Swinburne. Further along the east coast, there’s Shanklin and Sandown too.
