Holiday cottages for 2020 in Isle of Wight

Reserve your dream holiday cottage now for 2020 for just £30...Read more

Now's a great time to be sort next year's holiday plans. Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and get your 2020 holiday cottage set before someone else does. Plus, if you reserve your holiday now for just £30 we will reserve your dates until the 5th October when your full deposit is due. Tempted yet? Well here's a little more information about the promotion:

First thing's first; find your perfect property and preferred dates for your 2020 holiday. 

Then, click on "Book or Reserve Now" and enter a few details.

Once complete you'll receive a reservation confirmation email inviting you to opt into our £30 promotion. 

Then simply follow these easy steps to complete your booking or £30 reservation and then sit back, relax and enjoy your summer knowing you've got next year's covered!

From Cornwall to Dorset, Devon to Somerset and even as far as the Isle of Wight, take a look at our collection now and start dreaming of your next holiday with Classic Cottages. Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got 90 holiday cottages for 2020 you to choose from...

 

*Terms and Conditions:

The £30 offer extends your reservation until the 5th October when your full deposit is due and your booking confirmed. Prior to a full deposit our booking terms and conditions do not apply. 

Click here for full terms and conditions.

 

 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 90 Self catering holiday cottages for rent in 2020

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £373

2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £373

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. The double bedroom with pleasant views across the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

View
  • 10% off

    15 Sep 2019 - 21 Sep 2019

    £399.00 £359.10

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £393

2 bedroom, dog friendly self catering cottage in a rural setting close to Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £393

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £398

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £398

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £403

2 bedroom self catering apartment with sea views in Ryde.


8 Appley Sands is a spacious, purpose built, top floor apartment overlooking the Solent and the award-winning beach at Appley. With en suites to both bedrooms, and comfortable, mod...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £403

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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