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, 180 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, 331 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 riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading
4.98 out of 5 average rating, 451 reviews

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Charming, riverside log cabin on the bank of the Kennett, overlooking a nature reserve. Privately located in my back garden there is a large open plan room with 2 double sofa beds, sleeping 4, a slate bed pool table & Hi Fi system. There's a luxury en suite bathroom with copper bathtub, shower, basin & WC. There are basic kitchen facilities with kettle, toaster, double hot plate, microwave & grill, sink & refrigerator/freezer. A veranda with 2 bbq's & seats plus lower deck overlook the river.

Guest favourite
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, 235 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 Pigsty features a unique domed structure with a blend of dark and natural wood accents. A small outdoor seating area with a round table and two chairs is positioned at the entrance, surrounded by lush greenery and potted plants.
Hut in Winchester
4.98 out of 5 average rating, 635 reviews

The Pigsty

The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Top Guest favourite
Tiny home in Overton
4.97 out of 5 average rating, 481 reviews

Tranquil Garden Studio Retreat

- Stylish Garden Studio, enjoy birdsong, wildflowers 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
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, 259 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, 229 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
An open plan kitchen showcases a large wooden island with a smooth countertop, equipped with modern appliances. Pendant lights hang above, illuminating fresh flowers and kitchen utensils. The space transitions seamlessly to a cozy living area, visible through large windows that invite natural light.
Barn in Newbury
5 out of 5 average rating, 102 reviews

Stunning Parkland Barn Retreat

Maximum adults: 4 The Barn is set in beautiful private gated grounds on a quiet country lane, in an AONB. It is within easy reach of the A34 and M4, as well as the market towns of Newbury, Wantage and Hungerford. The nearest pubs are within easy walking / cycling distance. The River Kennet runs through the grounds leading to the canal and towpaths making visiting Hungerford and Newbury a pleasure by foot or bicycle. Fantastic rail routes from Newbury / only 50 minutes from London.

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, 121 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
The cottage exterior features a charming stone façade with a mix of brick accents. A gravel pathway leads to the entrance, bordered by lush greenery and trees. The roof is adorned with traditional slate tiles, complemented by a serene garden setting.
Cottage in Cirencester
4.95 out of 5 average rating, 247 reviews

The Old Bakery At The Grange

Perfectly located for RIAT, being walking distance from the Green Entry Point, The Old Bakery At The Grange is an ideal cottage for exploring all that the Cotswolds has to offer whatever the season. We are a few minutes’ walk away from The Old Spotted Cow pub. The cottage is full of country character and the interiors reflect our love of travel. Due to the character features of the cottage, it is unsuitable for very young toddlers and those unsteady on their feet.

Guest favourite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut in Ovington
4.97 out of 5 average rating, 165 reviews

The Glade at Ladyhill Vineyard near Winchester

Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Popular amenities for Winding Wood holiday rentals

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