Holiday houses in Winding Wood

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Top-rated holiday rentals in Winding Wood

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Top Guest favourite
A welcoming entrance is framed by a rustic wooden gate and lush greenery. The shepherd's hut is visible in the background, with a soft sunset illuminating the sky and reflecting off the structure. Pathways bordered by wildflowers lead towards the fields beyond.
Shepherd’s hut in Ewelme
4.99 out of 5 average rating, 621 reviews

Luxury Shepherd's Hut with stunning sunset views!

Welcome to Honeysuckle, our luxury shepherd's hut with stunning views across the fields in the Chilterns. In the evenings sit and watch the sun go down around your fire pit or stay cosy indoors with your log burner. We are a working farm and you may see the tractor trundle past feeding our herds of Texal sheep (Lambing right in front of you in March/April 2025!) and Limousin cows grazing in fields, or watch the many birds. You have your own secluded, fenced and private garden area with seating.

Guest favourite
A wooden cabin with an arched design is framed by tall trees, creating a natural setting. Steps lead to a spacious deck area, which includes potted plants and a dark wood BBQ grill under a covered space.
Tiny home in Buckinghamshire
4.97 out of 5 average rating, 816 reviews

The Woodland Cabin with Private Hot Tub Spa

Step into a world of peace and privacy in a secluded cabin. The perfect setting for romance, relaxation and a touch of luxury. Soak under the stars in the private hot tub, cozy up by the wood burner, the scent of countryside air and the sound of birdsong. With a comfy double bed, fitted bathroom, kitchenette, gas BBQ. Surrounded by scenic walking trails, charming pubs, and nearby heritage spots, this is the perfect romantic retreat to slow down, reconnect, and create unforgettable memories.

Top Guest favourite
The exterior of the cottage is presented, featuring a brick façade and a slate roof. Two windows adorn the front, allowing natural light into the interior. A small paved area is visible in front, furnished with two chairs and a table, in addition to well-maintained greenery.
Cottage in Peasemore
4.98 out of 5 average rating, 238 reviews

Beautifully renovated cottage - Prince's Forge

Prince's Forge is a newly converted cottage with its own private parking and courtyard garden, located on the edge of the downland village of Peasemore. It is situated on a quiet country lane, in an Area of Outstanding Natural Beauty (AONB), and has views across the neighbouring fields. It is within easy reach of the A34 and M4, and the local market towns of Newbury, Wantage and Hungerford. The nearest pub for good food and a drink is a short walk away and the local farm shop is close by.

Top Guest favourite
The exterior of a charming stone cottage is framed by vibrant flower beds. Two large windows allow light to fill the entrance, accented by a welcoming blue door. A lavender patch adds a pop of color in the garden, enhancing the cottage's quaint appeal.
Home in Oxfordshire
4.98 out of 5 average rating, 138 reviews

Cosy historic cottage near Cotswolds & Ridgeway

Stylishly decorated, spacious house in pretty Vale of White Horse village, southern edge of Cotswolds. Thoughtfully equipped and homely. Surrounded by stunning views to the Ridgeway. Great walking, village with pubs/deli/farm shop/groceries 1.5 miles away. Lovely pubs in surrounding villages. Open log fire. One king (en suite shower/WC), one double. Family bathroom/WC. Fabulous kitchen. Pets welcome, securely enclosed gardens. Friendly host. Great broadband. EV charger 100m away (cost).

Guest favourite
An open plan sleeping area features a spacious queen-size bed adorned with soft linens, surrounded by wooden accents and a collection of framed photographs. A small desk with a chair and flowers adds a touch of serenity, while a cozy seating arrangement offers additional comfort.
Cabin in Froxfield
4.92 out of 5 average rating, 223 reviews

Open Plan Barn near Hungerford and Marlborough

Nestled beside a manor house and surrounded by five acres of gardens, this sumptuous and comfortable open-plan barn offers a relaxing countryside retreat. Ideally located near the charming market towns of Hungerford and Marlborough, it provides the perfect base for exploring the local area. The barn is ideal for a couple or a single guest seeking a quiet and comfortable stay. In the morning, guests can enjoy a simple breakfast selection of cereals, bread, butter, jam and marmalade.

Top Guest favourite
Tiny home in Overton
4.97 out of 5 average rating, 458 reviews

Tranquil Garden Studio Retreat

- Stylish Garden Studio with picturesque garden and stunning views - Walkable from Overton station - Pubs, shops & local restaurants close by - Thoughtful touches, local gin, breakfast, fluffy towels - Fast WiFi, dedicated workspace & free parking - Dog-friendly, secure garden with resident, friendly dogs - Scenic walks from the doorstep - Escape from the city and immerse in nature - Close to Bombay Sapphire and Highclere Castle - Perfect for couples, dog owners and solo adventurers

Top Guest favourite
A spacious wooden deck is presented, featuring a mix of outdoor seating options, including a cozy sofa set and a round table with two chairs. The deck is surrounded by greenery, and a gentle overhang protects the sitting area, enhancing outdoor enjoyment.
Apartment in Berkshire
4.99 out of 5 average rating, 109 reviews

Cosy Rural Apartment

Kites Nest is charming and well appointed one bedroom apartment on the grounds of Hungerford Park, minutes from the town of Hungerford, a historic market town in the heart of the North Wessex Downs of Outstanding Natural Beauty and is surrounded by stunning countryside and picturesque villages. An ideal location for exploring Berkshire, Hampshire, Wilshire and Oxfordshire and within easy access to the M4 and Hungerford station which gives access to London Paddington.

Top Guest favourite
A contemporary studio apartment is positioned along the riverbank, featuring a modern design with large glass windows. A graceful weeping willow tree frames the scene, adding a natural element to the tranquil waterfront setting. Gentle ripples are visible on the water's surface.
Loft in Henley-on-Thames
4.94 out of 5 average rating, 211 reviews

Luxury Boathouse Apartment - central Henley

The Boathouse is a completely private studio apartment with wonderful river views. Furnished to a high standard with luxury bed linens and towels, and fully equipped with everything you could need. The perfect location for the Henley Royal Regatta, Henley Festival and The Rewind Festival Relaxing location that is perfect for watching the world and river go by, but also close enough to the hustle and bustle of the town and it's many restaurants and cafes.

Top Guest favourite
An open-plan living space features a cozy seating area with textured cushions and a coffee table. A well-equipped kitchen is visible in the background, highlighted by soft lighting and modern cabinetry. Natural elements, such as potted plants, contribute to a welcoming ambiance.
Barn in Gloucestershire
4.98 out of 5 average rating, 401 reviews

Luxury medieval barn in Cotswold town centre

Unique barn conversion nestled in a medieval alley in the heart of Fairford - open plan barn living with a snug living room and luxury bathroom. Climb the spiral staircase to the boutique bedroom or relax in the pretty, enclosed stone walled garden. We're next door to a lovely 15th century inn with a choice of other pubs nearby; Italian restaurant; local shops; pharmacy; cafes and takeaways on hand - a perfect base to explore this lovely part of the world!

Top Guest favourite
The exterior of a charming cottage is depicted, featuring a sloping roof and blue walls. Vibrant flower boxes with yellow and orange blooms adorn the windows, while a dark front door complements the overall design. A gravel pathway leads to the entrance, surrounded by greenery.
Bungalow in Tutts Clump
4.96 out of 5 average rating, 335 reviews

Garden Cottage..pretty countryside location

Our cottage is in a great little hamlet in Berkshire and is the perfect location for walking and exploring the countryside and the towns of Newbury and Reading.The cottage itself is open plan and is very light and airy with a modern mediterranean feel to it. It has two lovely bedrooms and two bathrooms. It is located in an area of outstanding natural beauty and is perfect for a quiet getaway or a busy shopping spree!

Top Guest favourite
A green wooden cabin is set within a spacious lawn, surrounded by tall trees. The cabin features a covered patio area with a table and chairs, while a white umbrella provides shade. Sunlight filters through the trees, creating a serene outdoor setting.
Guest suite in Highclere
4.98 out of 5 average rating, 124 reviews

Foxglove Studio

Lovely hideaway for the discerning guest - visitors to Downton Abbey, accommodation for local shoots or simply a base for those who wish to enjoy the wide array of local walks. The studio also lends itself to anyone who wishes to pitch a tent outside and enjoy a camp fire in the wood as the evening sun sets. Summer bookings June-September weekends two night minimum.

Superhost
Tiny home in Gloucestershire
4.92 out of 5 average rating, 276 reviews

Island | Private Lake Retreat + Hot Tub Escape

Island Lodge isn’t actually on an island, but it truly feels like one. Wake to lake views from bed, sunlight slowing you down before the day even begins. The deck sits so close to the water it feels like you’re floating, with kayaks for sunrise paddles and warm, quiet evenings by the log burner. Peaceful, simple and made for noticing just how still life can be.

Popular amenities for Winding Wood holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Berkshire
  5. Hungerford
  6. Winding Wood