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Holiday houses in Chillerton

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Top-rated holiday rentals in Chillerton

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Guest favourite
An aerial view reveals the grand historical Arreton Manor, featuring a distinctive red-tiled roof and a stone facade. Surrounding gardens display neatly trimmed hedges and lush greenery, while pathways guide the eye through the scenic landscape, creating a harmonious blend of architecture and nature.
Guesthouse in Arreton
4.99 out of 5 average rating, 73 reviews

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!

Top Guest favourite
A charming cottage exterior showcases a brick façade with a sloping roof. Large windows allow natural light to flood the interior. A gravel pathway leads to the entrance, bordered by potted plants. The surrounding green space adds a touch of nature to the welcoming atmosphere.
Cottage in Merstone
4.91 out of 5 average rating, 125 reviews

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

Top Guest favourite
Guesthouse in North Boarhunt
4.99 out of 5 average rating, 112 reviews

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.

Top Guest favourite
A private terrace features a small wooden table and two chairs, surrounded by greenery. Large glass doors reflect the garden's lush foliage, creating a seamless connection between indoor and outdoor spaces. Natural light illuminates the inviting area, enhancing the tranquil atmosphere.
Barn in Isle of Wight
4.97 out of 5 average rating, 251 reviews

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!

Top Guest favourite
The image features two rustic stone buildings surrounded by greenery. A gravel courtyard is visible in front, bordered by a wooden fence. Potted plants add a touch of color, while a tree line provides a natural backdrop to the serene setting.
Barn in Shorwell
4.88 out of 5 average rating, 130 reviews

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.

Top Guest favourite
Condo in Isle of Wight
5 out of 5 average rating, 18 reviews

The Garden Flat

Welcome to the Garden Flat, a tastefully refurbished studio apartment overlooking 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.

Top Guest favourite
A cozy bedroom features a double bed adorned with textured cushions and a patterned throw. Beside the bed, white nightstands with small vases are positioned, reflecting gentle ambient lighting from the wall-mounted fixture. Decorative mirrors enhance the room's inviting design.
Guesthouse in Isle of Wight
4.92 out of 5 average rating, 222 reviews

Studio 114- 1 bedroom guest house.

Cosy self contained studio next to, but separate to our family home located on the outskirts of Newport. 20 minute walk to the town centre and local amenities. 10 minute walk to the historic Carisbrooke castle and beautiful walks in the surrounding area. We are on a bus route. Private access to the property and free on street parking. Studio 114 offers a double bedroom, bathroom, kettle, toaster, microwave and mini fridge, TV, free Wi-Fi and small patio space with table and chairs.

Top Guest favourite
A charming brick building is seen nestled among lush greenery, with a gravel driveway leading to the entrance. The surrounding countryside features gently rolling hills under a cloudy sky, creating a serene and natural setting.
Cottage in Isle of Wight
4.99 out of 5 average rating, 204 reviews

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.

Top Guest favourite
Home in Gatcombe
5 out of 5 average rating, 14 reviews

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 .

Guest favourite
A decorative fountain with cascading water is situated in the foreground, surrounded by serene greenery. The wooden chalet, which features large windows, is visible in the background, alongside a wooden fence that encloses the outdoor space.
Farm stay in Godshill
4.85 out of 5 average rating, 119 reviews

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.

Guest favourite
Rolling fields are dotted with hay bales, leading to a view of coastal cliffs and the sea. A cluster of buildings is visible in the foreground, with a backdrop of clear blue skies and distant white cliffs along the shore.
Condo in Isle of Wight
4.91 out of 5 average rating, 139 reviews

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.

Top Guest favourite
Tiny home in Whitwell
5 out of 5 average rating, 10 reviews

Hannah’s Stable

Cosy one-bedroom holiday home set within a peaceful working stable yard beneath St Catherine’s Down, in an Area of Outstanding Natural Beauty on the Isle of Wight. Perfect for walkers and cyclists, with bridleways, footpaths and local pubs nearby. Includes kitchen, shower room, free parking and secure bike storage by arrangement. Meet our friendly animals too – Bambi the sheep, chickens and horses all call the yard home. Wightlink Ferry discount code available

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