Holiday Ideas > Best Winter Holiday

Best Winter Holiday


It is fair to say that sometimes a holiday during the winter months can be more needed than it is during the spring or summer. As the weather turns colder and the dark nights start drawing in, having a break from standard day-to-day life is a brilliant way to help you beat the winter blues. Of course, your trip as a whole will probably be more affordable with great ferry discounts too and the Isle of Wight is likely to be much quieter too, so it really is a win-win. 

When it comes to booking a winter getaway, you may find that you’re interested in staying in different towns and villages to where you’d head to during the warmer months. For example, staying right on the seafront in Sandown when it’s windy and raining might not be the best idea. So, to help anyone who is planning a winter holiday to the Isle of Wight, below are some of the best places you can stay on the island.


This is a quintessential English village and it is known for being home to the first-ever Isle of Wight Festival. In this picturesque village, you will find some of the oldest architecture on the island and when strolling down the charming main street in Godshill, you will find lots of traditional tearooms and small shops selling local produce. Due to its central location, this is one of the best places to stay on the Isle of Wight when you’re wanting to explore the whole island.


Many tourists head to Cowes during the warmer months, but it shouldn’t be overlooked during winter too. Located on the very northern tip of the island, this place to stay on the Isle of Wight can provide you with everything you could want for your holiday. At The Island Sailing Club, you will find a selection of cosy heated winter cabins situated beneath a canopy of fairy-lit trees and you can book to have dinner here, so it’s worth staying somewhere local just to experience this.


Situated on the South West coast of the island, Brightstone is a beautiful traditional village where you’ll find old farmhouses and thatched cottages. Not only is it within short driving distance of some brilliant tourist attractions, but this Area of Outstanding Natural Beauty has a number of footpaths and bridleways, so you can layer up and enjoy the incredible views. With lots of independent shops and eateries too, Brighstone is perfect for a winter getaway.


Whilst Ventnor is a traditional seaside resort on the South of the island, there is more to it than the beaches and promenade. When you head into the town, there are lots of vintage antique stores that have made it a popular shopping destination, and there are so many things to do whatever the weather. There are also brilliant performances around Christmas time at the Riddlestick Theatre at St Catherine’s Church in Ventnor too, so don’t miss these.


This is another smaller village and you will find it on the southwestern outskirts of Newport. This place to stay on the Isle of Wight is probably best known for being home to Carisbrooke Castle, but it is a brilliant central location for a winter holiday. There is a lot to do in both Newport and Carisbrooke and the surrounding towns and villages, no matter what your interests are, so you will never get bored when you choose to stay here.

Finding the best place to stay on the Isle Of Wight

Whilst your Isle of Wight holiday might be slightly different during the winter, it will still be really enjoyable nonetheless and you can trust that it will provide you with the break from normal life that you need. When deciding where to stay on the island, it goes without saying that if you choose any of the towns and villages mentioned above, you will be in the best place to enjoy everything that the island has to offer out of season.

  • Kingates Farm - Farm Cottage

    Prices from £299.00

    Character Farm Cottage sleeps 4 in two superking ensuite bedrooms (twin rooms on request). Enclosed dog friendly garden and private use of indoor pool with steam room. Stunning valley views with 2 acre walking paddocks, leading to AONB South Coast foot and cycle paths, award winning gourmet pubs and shops within a mile.

    • Enclosed dog friendly garden
    • Private use of an indoor pool
    • Return ferry from £41 return in Winter!
    • Direct access to foot paths
    • Low 20% deposit
  • Kingates Farm - The Stables

    Prices from £249.00

    This stunning barn conversion sleeps 2 adults has private use of a hot tub (additional £40 charge applies in "extras") and indoor pool with steam room. The enclosed dog friendly garden has valley views and 2 acre walking paddocks lead to AONB South Coast paths, several gourmet pubs and shops within a mile.

    • Private Hot Tub ("extra" charge)
    • Private use of indoor pool
    • Return ferry from £41 return in Winter!
    • Dog friendly enclosed garden
    • Low 20% deposit
  • Kingates Farm - Shepherds Hut

    Prices from £180.00

    Large traditional Shepherd's Hut sleeping 2, with attached ensuite "boudoir" bathroom, including private use of the indoor pool with steam room! 2 small/1 medium size friendly, adult dog/s (+12mths) free of charge with enclosed garden, 2 acre walking paddocks and stunning valley views! Optional Hot Tub being added in summer 2024, (discount to balance if NOT required)!

    • Private use of indoor pool
    • Return ferry from £41 return in Winter!
    • Direct access to footpaths
    • 2 small/1 medium size, friendly, adult dog/s welcome!
    • Low 20% deposit