Holiday houses in Chillerton

The Ocean Suite, Ventnor Beach (with Sauna)

Laid back beachfront living at its best, a romantic escape - popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner 2025 LUXLife Awards, Best Coastal Retreat, South England. 52 sq metres and open plan, with bi-fold windows/doors creating a beautiful space of just you and the ocean. With 2 private balconies, one south facing for sunbathing, the second with a private sauna, combine with a swim in the sea just a few steps away. No pets but baby welcome!

Location · Family · Parking

The Little Rose Pod.

Located on the outskirts of Newport "The Little Rose Pod" is the ideal base to start from if you want to explore the beautiful Isle of Wight or just get cozy and settle in and enjoy this romantic, rustic space that The Little Rose Pod has to offer. The area is quiet and peaceful and just a stones throw away from the main town and bus station, as well as being a short walk away from the historic Carisbrooke Castle and many picturesque cycle paths that lead to beautiful beaches and seaside towns.

Location · Value · Quiet

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

Family · Value · Outdoor spaces

Cosy Stable Cottage in the heart of the Island

PLEASE NOTE WE ARE NOT NEAR THE NEW FORREST NATIONAL PARK! This cozy cottage was the former Stables and lies in the grounds of the historic Merston Manor House dating back to 1605. The Cottage is approached by its own drive from Chapel Lane and has adjacent private parking. This cottage is next door my other listing Quaint Coach House Cottage which maybe available if this is not. We have a minimum 3 night booking but can be flexible on request. Monday night is not available except on request

Location · Family · Heating

Little Wing peaceful barn with garden/parking

Little Wing is a beautifully converted studio apartment (originally a milking parlour for goats) located in a peaceful, rural village- 'Best Kept Village' on Isle of Wight 2025 - in the heart of an Area of Outstanding Natural Beauty. Including a large, super-king size bed, the open plan contemporary design is perfect for couples looking for a quiet or romantic retreat and the patio and private garden are perfect for summer relaxation, while underfloor heating means even winter days are cosy!

Family · Location · Cleanliness

One bedroom cottage escape

Relax and make yourself at home in our charming 1-bedroom bungalow — the perfect retreat for a restful getaway. Featuring a super king-size bed with White Company bedding, a well-equipped kitchen and a bright and comfortable living room with stunning views of the garden. The modern restroom includes a walk-in shower and Rituals toiletries for a luxury experience. Enjoy your morning coffee on the patio or take advantage of the hammocks on the pond both with views of the surrounding garden.

Location · Family · Checkout

The Loft Flat

Welcome to our bright open plan Loft Flat, which is tastefully furnished, and overlooks a beautiful garden and stream, which you are welcome to wander round. Located in the attractive village of Carisbrooke, it’s an ideal location for exploring the Island. It’s five minutes walk from Carisbrooke Castle, and ten minutes walk from the Tennyson Trail, which leads to Tennyson Down, the Needles, and the sea. There is picturesque countryside on the doorstep, an area of outstanding natural beauty.

Location · Comfort · Cleanliness

Hidden Away Converted Barn Loft in Shorwell

Northcourt Farm is situated in a valley on the edge of chalk down land, surrounded by pastureland and Grade II Listed Parkland, because of its historic link to Northcourt Manor (privately owned). It's home to our horses, dogs and occasionally some sheep. There are just two dwellings on the farm, our farmhouse cottage and The Barn Flat. The Barn Flat would appeal to walkers and cyclists, having access to the Tennyson Trail, with several paths/bridleways running across our farmland.

Location · Family · View

Converted barn perfect for families and couples

At the base of Rowridge Valley in the heart of the Isle of Wight countryside. You will find The Piglet, a great place to stay, relax and use as a base to explore the island. A cosy building with a sunny aspect and a private garden to the rear that overlooks the neighbouring countryside. Due to its location most of the island is accessible from here within a short drive. Explore the heritage castles & monuments, the beaches & surf, and family friendly parks throughout the island.

Family · Location · Comfort

Tuckers Farm | Luxury rural retreat w/ games space

Tuckers Farm is a detached farmhouse built in 1640, from its own (now disused) quarry, brimming with character, set within 15 acres of private rolling fields and landscaped gardens. With a heated saline pool, a games barn, multiple entertaining areas, and panoramic views, it offers the ideal backdrop for unforgettable stays. Perfect for a family gathering, retreat, milestone celebration, wedding, or accommodation for a wedding in neighbouring Gatcombe Estate Vineyard .

Family · Location · Quiet

Foodies Heaven

A light and airy wooden chalet accessed by a path through a fully fenced orchard with seating and a fire pit ideal for catching the last of the evening sun. Dogs are welcome and can be walked within the 8 acres of farmland which extends to the Eastern River Yar and includes a wildlife pond. The chalet is well equipped with a dishwasher and washing machine. If you’re lucky you’ll wake up to a Red Squirrel. 5 Pygmy goats in Sue’s garden next door are sure to amuse you.

Value · Location · Air conditioning

Chale Bay Farm - Tennyson View

A fabulous stand-alone air-conditioned room with ensuite bathroom and private front door, ideal if you want a room only and to eat out or booking alongside our main self- catering apartments for extra friends & family. Mini-fridge, tea & coffee, smart TV, Blu-ray & WiFi. Super-king bed, sofa, armchair and ample wardrobe/drawer space. French windows look onto the personal patio with chairs and stunning sea and countryside views towards Tennyson Down and the Needles.

Value · Family · Checkout