Holiday houses in Winding Wood

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Top-rated holiday rentals in Winding Wood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Goring
4.98 out of 5 average rating, 179 reviews

Pool House at Mill Cottage

The Pool House at Mill Cottage offers a unique riverside escape with exclusive access to a private pool (Mar 1st - Oct 1st 2025 & Apr 1st - Oct 1st 2026). Nestled on the Thames, enjoy easy access to riverside cafes and restaurants by foot or boat. The charming one-bedroom retreat features blackout blinds for restful nights, plus a small sofa bed for extra guests. Just minutes from Goring on Thames village and the train station, it also boasts a BBQ and outdoor seating area for relaxing evenings.

Top Guest favourite
A spacious room features a king size bed with light blue bedding. A small dining table is positioned nearby, complemented by rattan seating. A kitchenette with a microwave and fridge is visible, along with a TV. Natural light filters in through two windows.
Guest suite in Kintbury
4.87 out of 5 average rating, 330 reviews

The Pottery Barn

This is a self contained annex above a double garage (please note low roof angles in places) with an independent door. It has one king size bed with some seating and a TV and dinning table. There is a small kitchenette including a microwave, fridge, kettle and toaster. The ensuite has a basic electric shower and usual amenities. There is internet available. If you would like to bring a child please contact us before to check if suitable. There is parking on the main road or opposite in a Close.

Top Guest favourite
A spacious bedroom is furnished with a king-sized bed, complemented by coordinating bedding and decorative pillows. A comfortable sofa is situated near large windows, allowing natural light to flood the room. A table with two chairs is positioned for dining or work purposes, enhancing functionality.
Apartment in West Berkshire
4.95 out of 5 average rating, 213 reviews

"The Retreat" at The Fox at Peasemore Country Pub

The "Retreat" at The Fox at Peasemore is a lovely, relaxing, quality self-contained apartment. It has its own private entrance, the added bonus being, it is attached to an award winning & highly rated country pub. (See our website for our reduced trading hours). Set in the beautiful rural village of Peasemore, 6 miles from Newbury (The U.K Crossroads) just a 30 minute drive to Oxford or Marlborough, 15 to Highclere Castle. Fully fitted kitchen, Pod coffee machine and NETFLIX on the flat screen

Top Guest favourite
A generous living space features a large stone fireplace with a wood-burning stove at its center. Two comfortable armchairs are positioned adjacent to a spacious sofa, creating a cozy seating area. Soft lighting from table lamps complements the warm tones of the decor.
Cottage in Gloucestershire
4.99 out of 5 average rating, 214 reviews

Chic Georgian town house in Cotswold town centre

Chic luxury town house full of charm with river views. Formerly the town's Post Office, in the heart of Fairford. Three boutique luxury bedrooms, one with master en-suite. Large fully equipped kitchen, generous living space with large fireplace. 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.

Superhost
The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn in Great Milton
4.95 out of 5 average rating, 234 reviews

17th Century Barn in quiet country village

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

Top Guest favourite
The exterior of the larch clad Annexe features modern vertical wood paneling. Large glass doors lead into the entrance, framed by two planters with lush green grass. A gravel path provides access, highlighting the contemporary architecture amid a clear blue sky.
Home in Cirencester
4.98 out of 5 average rating, 258 reviews

Larch clad architect designed contemporary annexe.

Relax at this unique and tranquil getaway in the beautiful South Cotswolds. The Annexe is a separate dwelling next to an architecturally award winning contemporary house located in a quiet village. The larch clad property has an industrial, boho meets the Cotswold vibe with its own private wild flower garden, perfect for alfresco dining. Excellent location for walking, running and cycling. Close to the beautiful town of Cirencester, idyllic picturesque villages and gastro pubs galore!

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, 226 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
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, 120 reviews

Kites Nest - 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
Barn in Ecchinswell
4.93 out of 5 average rating, 391 reviews

The Pigsty

Escape to a tranquil rural setting in the heart of the Hampshire countryside and in the shadow of Watership Down. Beautiful self-contained accommodation surrounded by gardens in a historic village with easy access to a multitude of walks and local amenities. Nearby attractions include Highclere Castle, Greenham Common, Stone Henge, Newbury and Winchester. Oxford (35 miles), Bath (70 miles) and London 45 minutes on the train from Newbury or Basingstoke.

Top Guest favourite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guesthouse in Garsington
4.95 out of 5 average rating, 542 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Top Guest favourite
Guesthouse in Childrey
4.9 out of 5 average rating, 208 reviews

Stylish country converted barn

Symonds Barn is a spacious converted barn set in the middle of Childrey, a village on the edge of the Ridgeway, only 15 miles from Oxford. Choose between enjoying an escape to the countryside, with delicious meals in one of the many local cafes and pubs and walks through some really beautiful countryside (it’s a 5 minute drive onto the Ridgeway), or take advantage of the nearby shopping and culture in Oxford, Marlborough, Hungerford or Burford.

Guest favourite
Home in Berkshire
4.93 out of 5 average rating, 109 reviews

Charming period home in historic Newbury

Welcome to our cosy home in central Newbury. Perfect for Highclere castle and Just a 3-min walk to the town centre and Train station, walking distance to Newbury racecourse, ideal for exploring local shops, cafes, and the River Kennett. Enjoy countryside walks, cycling, and shopping nearby. Two bedrooms, 2 Bathrooms, Dining room, Private garden, Fast Wi-Fi. Pets welcome. Easy rail access to London, Oxford, Cotswolds. easy access to the M4.

Popular amenities for Winding Wood holiday rentals

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