Holiday houses in Whippingham

Self Catering Annex 2 separate beds (1 bedroom)

⛴️ 0.4 miles from the ferry, Castle Copse Annexe is a lovely compact modern self catering property situated in a quiet housing estate and named after the small copse, a few minutes walk away. Walk through the copse, and it will lead you to the town centre, where you will find shops, cafe's, pharmacies, and supermarkets. It is a 10 minute walk to the beach & crossing to Cowes. The annexe is only suitable for a max of 2 persons and unsuitable for small children due to the stairs, & sofa layout.

Cosy Cabin with Private Hot tub | Isle of Wight

Modern purpose built self contained chalet, next to the house but with its own private entrance and private pergola area with canvas sides complete with cosy seating & lighting plus hot tub! Situated in East Cowes. The house was part of the Osborne estate so we are situated right next to Osborne House, also a 2 minute drive or 15 minute walk from East Cowes Red Funnel. We are also on a main bus route to Newport or Ryde. There is private access & your own parking space. It is an ideal location.

Beautiful Spacious Victorian Town House in Cowes

This beautiful spacious 2 bedroom town house is located on a quiet street a few minutes walk from the town centre. The whole property has been recently decorated giving a fresh light feel & furnished with a lovely seaside theme. Cowes town centre is just a few minutes walk away with its excellent selection independent shops and restaurants. Just beyond the town is the seafront which takes you along the beautiful esplanade passed the Royal Yacht Squadron and on to Gurnard famous for its sunsets

Stylish apartment with sea views - Cowes

Lorne Villas Apartment Contemporary and spacious first floor apartment with sea views, just minutes from Cowes' vibrant High Street, the Red Jet ferry terminal, the Esplanade, and local beaches. With a variety of pubs, eateries, and yacht clubs nearby, it's the perfect base for exploring Cowes and beyond.​ *Ferry discounts up to 35% available* Accessibility Note: Pls be aware that the internal steps are steep and narrow, making the apartment unsuitable for guests with restricted mobility.

Cowes 2 Bed Apartment, Heart of the Action

We think our place is really special. In the centre of Cowes with everything on the doorstep makes it convenient and so easy with everything walkable. We love being part of the atmosphere of the world famous Cowes. We have two bedrooms, one with a lovely big cosy super king the other is a double with a single bunk above it. The fully equipped kitchen is modern and equipped with everything you need along with the furnished living / dining room with TV and fast internet access.

Riverside Mews is ideally located with sea views.

Riverside Mews, 5 Seymour Court is right on the River Medina with far reaching views across the Solent. The floating bridge is steps away from the front door and you can hop on it for a few pennies to reach West Cowes. Here you will find a plethora of shops and restaurants all busy with tourists and sailors. Cowes is a mecca for the sailing community and yachts can be seen at all times of the year. Seals have also been seen bobbing up and down just outside the house !

Seaside style cabin in central Cowes

'The Cabin' sits in the heart of West Cowes, tucked away behind the high street. Very compact (and very cute!), the space is kitted out in classic holiday home style. Two bedrooms and a sofa bed. Shower room. Decked garden with dining table, BBQ and outdoor sofas. Free parking space nearby. Fast broadband (free), digital TV with DVD, washer/dryer, dishwasher, microwave. Welcome breakfast for first day included. Good for families but steep steps to access. Book today!

Field View Cabin

This stylish modern place to stay is perfect for a great getaway. The cabin is situated on the owners property, set back from a main road. However it has its own separate/private entrance and parking. The Cabin is designed so that the accommodation windows and private patio/sitting area all face the fields. Located centrally on the Island, less than 1 minute walk to bus access and local family friendly pub. Also a short walk to river-side cycle track.

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.