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!

The Nook, Arreton Manor, Isle of Wight

Welcome to The Nook, your little haven nestled just below the Arreton Down Nature Reserve, your home away from home in our historical Arreton Manor. The Nook is beautifully airy with wonderful, high A-lined ceilings spanned by old heavy oak beams with large windows overlooking the gardens. You will have a private guest suite which is comprised of a bedroom, shower room, kitchenette, living area, patio and Hydropool hot tub. Expect soft towels and cosy bedding. We want you to relax and revive!

Pretty cottage in lovely area near south coast

WARM, COMFORTABLE, AMAZING LOCATION A super-cosy, rural getaway with an unbelievable view, set in the grounds of a medieval manor but feels private. Perfect for a family, a couple, friends. Looks out onto a lake and the downs. 10 mins to the coast, within 30 mins to anywhere on the island - village pubs, seaside towns, foodie restaurants, beaches, adventure parks, castles, cliff-top walks. An incredibly peaceful and restorative haven for 2 to 4 people. A very tranquil yet very handy location.

Quaint Coach House Cottage in the heart of the IOW

PLEASE NOTE WE ARE NOT NEAR THE NEW FORREST NATIONAL PARK! This pretty cottage was the former Coach House and lies in the grounds of the historic Merston Manor House which dates back to 1605. The Cottage is approached by its own drive from Chapel Lane and has private parking opposite. This cottage is next door my other listing Cosy Stable Cottage which maybe available if this is not. We have a minimum 3 night booking. Monday is not available but please contact me if you require a Monday stay

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.

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!

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.

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.

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 .

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.

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.

Cosy underground burrow with countryside views

Welcome to your cosy home from home in one of our three beautifully crafted retreats, discreetly nestled into the gentle slope of Bennetts Rock, with sweeping views across the Lower Valley and the Downs beyond. Our one bedroom burrow is thoughtfully designed to offer comfort, warmth, and flexibility - perfect for couples, small families, or friends seeking to unwind in comfort after an evening of live entertainment at one of the park’s many celebrated events.