Holiday rentals in Whippingham

Sea Views, Blue Winds, Newly Renovated, Cowes Town

A quirky coastal flat with sea views across the Solent in the heart of West Cowes. With a top look out room and balcony which is amazing in both summer and winter :) Just 2 minutes walk from all the amenities of Cowes town centre, the marina and Red Jet to Southampton, and just a short walk to the beaches. Discount for the car ferries available! *Locked outside area for bikes Why not use a popular search engine to see our reviews, search for Blue Winds and Waves, Cowes to see more about us.

The Garden Wing is a very special tranquil place

This unique place has a style all its own. Designed in a Japanese way with it's own Water Garden, terrace and boardwalk. Ideal for a family and children will love The Garden Wing, but there is access to the Japanese water garden, and bedroom 3+4 have unguarded stairs to unuseable mezzanine bunks ( see photos). If in any doubt about suitability.....please message me before booking. It is perfect for 6 people, but has beds for 8 EV charger. Oct-Mar + Midweek availability message me first please

Cosy Self Catering Annex 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.

Albert’s Dairy Cottage, Whippingham

Albert’s Dairy Cottage is a beautifully converted one bedroom cottage situated adjacent to open countryside. The contemporary design offers spacious accommodation, is finished to a high specification and offers the perfect environment for couples looking for a relaxing break away. Conveniently situated less than 10 mins from both the Red funnel and Wightlink car ferry terminals, the property is ideally located for exploring the Island, is close to the River Medina and popular waterside pubs.

Harbour Cottage Your Romantic Getaway in Cowes

Harbour Cottage - perfect romantic getaway. Close to the centre of vibrant Cowes with local independent shops, cafes, restaurants and marinas. You can leave the car at home! Minutes from Red Jet terminal, floating bridge and Shepards Marina. Generous ferry discounts enquire on booking Harbour Cottage is great for short breaks, or longer stays. Fully fitted kitchen, lounge, conservatory, bathroom and bedroom with king size bed and small sofa fold out ideal for child or small adult only

Cosy Cabin with Private Hot tub | Isle of Wight

Modern purpose built self contained cabin, 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 20 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. CCTV on driveway.

Marina View Flat, Ferry Discount and Parking

What a find! One bedroom flat (a second room is locked for storage) with Parking for one car no vans, sleeps 2/3 people in one double bed and a third person on the pull out big mattress Jay bed in dining room.. Third person to be agreed, small extra fee per night £35 Fab river view with balcony. A lovely restaurant and bar 3 mins walk Top Floor no lift. Three flights of stairs Outdoor videocam security. Cat stays on property when I take the whole flat to myself if any allergies.

Ocean and sky at your doorstep

Nestled in the picturesque Gurnard, Cowes, The Beach Shack offers a rare opportunity to experience the best of coastal living. Located right on the seafront, this contemporary beach house combines comfort, style, and unbeatable views, making it the perfect getaway for those seeking relaxation by the sea. Whether you’re enjoying the vibrant atmosphere of Cowes or unwinding with the sound of waves crashing at your doorstep, The Beach Shack is the ultimate seaside retreat.

Romantic Treehouse for 2

Welcome to The Nest Treehouse — a stylish and relaxing Isle of Wight escape designed for slow mornings, coastal adventures, & peaceful evenings after a day exploring the Island. Perfect for couples, solo travellers, 1 child families , for weekend getaways, short stays or summer holidays, the Nest Treehouse combines stylish interiors with everything you need for a comfortable stay in one of the UK’s most loved holiday destinations. GOOD FERRY DISCOUNTS - please ask.

Riggers Rest, Stylish Renovated Home with Parking

Riggers Rest has been completely renovated to a very high standard, creating the perfect home‑from‑home in the heart of Cowes. With 3 gorgeous bedrooms, a brand‑new family bathroom and an en‑suite shower room, this stylish property offers comfort and convenience for up to 6 guests. The open‑plan lounge and dining room feature a cosy log burner, and the new kitchen opens onto a lovely garden. Private parking completes the package, a rare find in central Cowes.

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.

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 also a short walk to river-side cycle track.