Cottages Sleeping 7 People on the Isle of Wight
Blend amazing adventures, a beautiful setting and luxury accommodation and you have a fantastic combination. Add a bunch of your close friends and family to share it with, and it's even better. At Classic Cottages we have 51 self-catering cottages sleeping seven people available on the Isle of Wight for you to share with your favourite people. Pack your bags and let the good times roll.Read more
Looking for a large holiday cottage that sleeps seven or more? Our spacious retreats on the Isle of Wight are ideal for family holidays or for an escape with a group of friends. Pick a cottage with a hot tub, or choose one with incredible sea views. If you've got a foodie in the gang, pick a cottage with a barbecue, or if you've got your dog with you, choose from our selection of properties with enclosed gardens. However you envisage your dream holiday and whenever you'd like to go, a holiday on the Isle of Wight with your friends and family needs no excuses.
Stay in a Self-Catering Cottage for 7 on the Isle of Wight
We go to great lengths to make sure each of our luxury self-catering cottages is superbly equipped. We want you to feel at home straight away, which is why everything you and your group could need and more is provided. From real beds, to fluffy towels to your morning coffee pot, we will make sure your stay is as comfortable and relaxed as it can be.
If you can't wait to book the holiday of a lifetime, browse our selection of available cottages. Or, if you'd like to ask us a few questions, don't hesitate to get in touch.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
Choose from 51 cottages that sleep 7 on the Isle of Wight
7 nights from £454
Ashmead Cottage
37233 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight
If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...
7 nights from £454
7 nights from £555
Dickens Cottage
35914 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...
7 nights from £555
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £696
Keepers Cottage
40704 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight
This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...
7 nights from £696
7 nights from £850
Montagu Apartment
36343 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.
Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...
7 nights from £850
7 nights from £548
Alcantara
35743 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation in the heart of Seaview. This detache...
7 nights from £548
7 nights from £555
Fernfield
36013 bedroom, Rural holiday cottage with sea views in Brook, Isle of Wight
This pretty detached cottage can be found on a quiet lane in Brook on the south west coast. With its large, mature garden overlooking adjacent farmland, and close proximity to mile...
7 nights from £555
7 nights from £571
Lucaya
36214 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...
7 nights from £571
7 nights from £586
Crowsteps
37364 bedroom self catering apartment near the beach in Seaview.
Crowsteps is on the first and second floor of a semi detached property tucked away in Seaview. Boasting a stunning roof terrace with far reaching views over the Solent, where you c...
7 nights from £586
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 £589
House of Logs
42254 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...
7 nights from £589
7 nights from £657
Middle Salterns
36314 bedroom, self catering cottage near the beach in Seaview, Isle of Wight.
Middle Salterns is a pretty, end of terrace Edwardian property in the heart of Seaview, simply decorated and arranged over three floors. There are two double bedrooms and a bunk-ro...
7 nights from £657