Holiday rentals in Five Hundred Acre Wood

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Top-rated holiday rentals in Five Hundred Acre Wood

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Top guest favourite
A modern, black-clad building is set within a spacious gravel area, surrounded by neatly trimmed greenery. A covered outdoor dining area is visible, complemented by potted plants. The sky is bright with scattered clouds, creating an inviting atmosphere for relaxation.
Cottage in West Sussex
4.99 out of 5 average rating, 145 reviews

Architect's Upscale Hay Barn Conversion in Rural Sussex

Scandinavian influences inspire the open and bright interior, which blends in seemlessly with the paved terrace around the building. At the entrance of the building is a ca. 70cm deep decorative pond with water-feature, adding to Nettle Fields’ tranquil and relaxing setting. The hosts Michael & Toby and their dog Heidi live in a barn conversion at 50m distance and can help with anything you may require during your stay. Follow us on Instagram @Nettlefields; Michael is @michaelkopinski and Toby @tobschu. Nettle Fields is surrounded by a 1-acre garden plot. Several footpaths are nearby, leading to pubs, gardens, and a hotel with a new spa. Nearby Horsham offers everything to be expected from a pretty English market town. Brighton is 20 minutes by car. Since the property is in rural Sussex, it is best to have a car at one’s disposal. However, short distances to venues such as Leonardslee and South Lodge can easily be reached on foot or by a 5-minute taxi ride.

Top guest favourite
A shepherd’s hut is positioned in a grassy area, with wide doors open to the exterior. An alpaca is seen grazing on the lawn, surrounded by lush greenery under a clear blue sky. Outdoor seating is visible nearby, inviting relaxation in nature.
Shepherd’s hut in East Sussex
5 out of 5 average rating, 124 reviews

The Woolly Retreat - Alpaca Shepherds Hut.

Nestled in a secluded Alpaca field in the heart of the enchanting Ashdown Forest lies a cosy, new Shepherd’s Hut in the idyllic village of Hartfield, famous for its connection to Winnie the Pooh and his timeless adventures. Surrounded by Alpacas which you can feed , this charming retreat offers a perfect blend of rustic luxury & nature. Whether you're looking for a romantic getaway, or just a relaxing weekend immersed in nature, our shepherd's hut is the place to unwind, recharge and reconnect.

Top guest favourite
A spacious living area is highlighted by large windows offering views of the surrounding greenery. A comfortable sofa and an ottoman complement a soft area rug. A television and a small lamp add functionality, while houseplants contribute to the relaxed ambiance.
Apartment in Blackboys Near Uckfield East Sussex
4.98 out of 5 average rating, 170 reviews

Peaceful spacious country barn with amazing views

Gunbanks Farm TN225HS is in the heart of the Sussex countryside in an area of outstanding natural beauty. It is a peaceful retreat to escape the stress of daily living. Tucked away down a private drive with easy parking. There is an outside space to sit and relax. The barn is spacious and sociable. There is a working forge just by the barn. Occasionally there will be farriers making shoes and wrought iron pieces. You will see evidence of this around the garden with beautiful horseshoe balls.

Guest favourite
A charming wooden lodge is nestled among lush green trees, featuring a sloped roof and welcoming wooden deck. Large windows allow natural light to fill the interior, and the entrance opens directly into a spacious and inviting living area. Surrounding greenery enhances the tranquil setting.
Cabin in East Sussex
4.97 out of 5 average rating, 105 reviews

Goldcrest Lodge Wadhurst

Goldcrest Lodge is a peaceful hideaway within secluded woods on the 140 acre historic estate of Wadhurst Castle. It is designed to blend in to its woodland setting, yet is bright and spacious with modern luxuries - perfect for a romantic break, a restful escape or for reconnecting with nature. It has a double bedroom (5' bed) with huge picture window, a central main room with sofa bed leading to a kitchen area and separate shower room beyond. Decking and private screened bath. Dog friendly.

Top guest favourite
A comfortable sleeping area features a king bed with dark throw blankets and decorative pillows. Flanking bedside tables hold stylish lamps. Artwork adorns the walls, while a small window allows natural light to enter, providing a view of the outdoor greenery.
Guest house in East Sussex
4.95 out of 5 average rating, 110 reviews

Double room in detached annex

Self contained double room in our detached garden annex with private off road parking and EV charging nearby. Equipped with a king bed, TV, waterfall shower and separate WC, hair dryer, kettle and mini fridge. Outside space with table and chairs for al fresco dining! Located close to the Ashdown Forest with plenty of country walks. We are a 15 minute drive from Royal Tunbridge Wells and an hour from London and the East Sussex coast. We are on hand in the main house for your convenience.

Top guest favourite
A frost-covered lawn is framed by a wooden fence, leading to a view of two charming houses nestled among trees. The scene is set under a clear blue sky, with colorful autumn foliage enhancing the landscape.
Cottage in East Sussex
4.96 out of 5 average rating, 186 reviews

The Cottage, Dovedale Farm, Crowborough, TN6 1UT

This beautifully presented two bedroom detached cottage is situated within close proximity of Crowborough Town Centre and approximately 7 miles from the vibrant heart of Tunbridge Wells with popular shops, bars and restaurants. This characterful property is set amongst 4 acres of mature landscaped gardens which encompasses a private fishing lake. Along with 2 double bedrooms, this separate annex also comprises its own courtyard garden, ample parking as well as stunning views of the garden.

Top guest favourite
A sunny view of the property surrounded by lush greenery and vibrant shrubs. The gravel driveway leads to the barn, framed by well-maintained grass. A seating area with minimalistic chairs sits on the lawn, inviting relaxation amid a serene natural setting.
Barn in Nutley
4.98 out of 5 average rating, 204 reviews

Rural Retreat on the Ashdown Forest

THE FOREST MALTHOUSE on the Ashdown Forest is a luxurious, spacious, detached, 1 bedroom, converted barn dating from 1822 with wonderful views over the forest. The Vaulted Oak Framed barn offers guests an extremely high standard of countryside self-catering accommodation with endless walks on your doorstep & a large, open plan kitchen & living/dining room. In a quiet, rural setting, with secure gated parking it's an ideal base for walking, cycling, fishing, bird watching or simply relaxing.

Guest favourite
Rooftop space is equipped with a circular hot tub and several wooden chairs with cushions. Soft lighting from string lights creates a relaxed ambiance, while the surrounding trees and open field provide a natural backdrop.
Tiny home in Furner's Green
4.88 out of 5 average rating, 104 reviews

Delightful Double Decker Bus with Hot Tub sleeps 4

Unique Stay in a fabulous converted DOUBLE DECKER BUS! Unwind in the rooftop Hot Tub after a day of wandering the Bluebell Woods, playing Crazy Golf on site, exploring the nearby Ashdown Forest or the local Vineyard for Wine Tasting or enjoying the onsite Ice Cream parlour. The bus boasts a super comfy double bed downstairs and European sized bunks up top! Heating upstairs & Down, as well as heated blankets to keep it nice and cozy in the colder months! Over 16s ONLY June through August

Top guest favourite
The entrance area features a private courtyard with a set of metal bistro chairs and a small table. Lush greenery decorates the space, with potted plants placed around the outdoor area. The inviting door leads into the cozy retreat.
Cottage in Duddleswell
4.99 out of 5 average rating, 302 reviews

Hundred Acre Studio, an Ashdown Forest retreat

Hundred Acre Studio is a charming retreat down a private track on the Ashdown Forest. In the heart of Winnie the Pooh country, it is a perfect base for exploring the many pubs, beautiful walks, vineyards, heritage railway, and National Trust properties in the area. Close to the South Downs and the coast, as well as nearby Tunbridge Wells with its historic old town and weekly summer jazz nights. It is the ideal country getaway; private, quiet, and with everything you need for a break.

Top guest favourite
The exterior of The Hideout is visible, showcasing large glass doors that provide a view of the interior. Surrounded by lush greenery, the space is framed by vibrant flowers and plants, highlighting its connection to nature. The wooden structure features a sloped roof, blending with the environment.
Cottage in East Sussex
4.92 out of 5 average rating, 284 reviews

The Hideout - in the heart of Ashdown Forest

The Hideout is located down a private drive, well off the road and right on Ashdown Forest. We are a five minute walk from Gills Lap which is a central walking hub on the forest. Dogs are welcome and there is a secure, enclosed courtyard garden. You can walk for miles from the gate and we provide maps and walking suggestions. Forest Row, a ten minute drive, provides good shops, restaurants and cafes. There is a great local pub, The Hatch Inn, which is walkable during daylight hours.

Guest favourite
A comfortable living area features a light grey sofa with green accent pillows facing a wall-mounted television. Two stylish floor lamps stand next to the windows, which provide views of the surrounding nature. The wood flooring complements the earthy tones of the brick wall.
Barn in East Sussex
4.94 out of 5 average rating, 112 reviews

Entire converted stone coach house

The Coach House is a newly converted, open plan space with very good internet connection in tranquil wooded location on the edge of the Ashdown Forest. It is adjacent to, but detached from the main house Fairstowe and is ideally suited for family occupancy or a couple. Guests have the freedom of having sole occupancy. A 2nd bedroom can be created by closing a multifold door where a single regular bed is provided for one guest and a single fold-out bed is available for a second.

Top guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 845 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Popular amenities for Five Hundred Acre Wood holiday rentals