Holidays Cottages Sleeping 9 People on the Isle of Wight
Our specially chosen cottages sleeping 9 people on the Isle of Wight are perfect for a group holiday. Enjoy a short break or spend a couple of weeks unwinding and catching up, the choices are yours. Whether it's to celebrate a birthday or just an excuse to get together, a holiday on the Isle of Wight will create wonderful memories for you all. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Discover our collection of 15 cottages sleeping 9 people
7 nights from £
2 Little Cedars
35204 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...
7 nights from £
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25% off
11 Jul 2025 - 18 Jul 2025
From £2220.00 £1665.00
7 nights from £840
6 Seafield Terrace
35625 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...
7 nights from £840
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 £1157
Creekside
35884 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...
7 nights from £1157
7 nights from £1728
Pepita
57195 bedroom, dog friendly holiday cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1728
7 nights from £1176
Orchard House
36414 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight
Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...
7 nights from £1176
7 nights from £1370
Saye House
45734 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...
7 nights from £1370
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40% off
5 Jul 2025 - 11 Jul 2025
From £2436.00 £1461.60
7 nights from £1404
Pitt Corner
36444 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is a roomy retreat, with plenty of space for the family to spread...
7 nights from £1404
7 nights from £1773
Harbour View
47314 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...
7 nights from £1773
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.
7 nights from £1806
Windy Ridge
44644 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...
7 nights from £1806
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20% off
1 Aug 2025 - 8 Aug 2025
£3110.00 £2488.00
7 nights from £2008
Solent Heights
39465 bedroom self catering cottage near the beach in Cowes, Isle of Wight
A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...
7 nights from £2008
Escape for a while and take your friends and family with you, the Isle of Wight is calling. The best way to catch up on lost time is to get away together for a while.
Isle of Wight Self Catering Cottages Sleeping 9
Whether you would like to take a short break together or enjoy a longer holiday to really kick back, our Isle of Wight holiday cottages offer the perfect base for a group getaway. From country to coast, we provide cottages of all shapes and sizes ready to welcome you all. Many are dog friendly too, meaning the whole family can get involved.
With every one of our holiday cottages carefully selected and personally inspected, we make sure only the best are on our books. Once you have chosen the cottage of your dreams, you can relax knowing that everything is taken care of for you. All of our cottages are fully equipped, from the kettle to the towels. All that you have to do is relax and catch up with the ones you love most.
