Holiday houses in Five Hundred Acre Wood

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Top-rated holiday rentals in Five Hundred Acre Wood

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Guest favourite
An alpaca stands near a round fire pit with embers glowing in the center. In the background, a shepherd's hut is visible, featuring a small door and chimney. Trees line the area, providing a natural setting.
Shepherd’s hut in East Sussex
4.99 out of 5 average rating, 149 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 charming houseboat is nestled on a tranquil lake, surrounded by lush greenery and golden leaves. The exterior features wooden paneling and large windows that reflect the serene water. Lilypads cover parts of the lake, enhancing the natural beauty of the setting.
Guesthouse in East Hoathly
4.93 out of 5 average rating, 182 reviews

Romantic Floating Cabin -‘The Water Snug’

Romantic lake cabin for two, floating on our peaceful one-acre lake in ancient woodland. Relax by the cosy log burner, cook in the fully fitted kitchen, and wake to magical lake views from the bedroom. In spring, enjoy the woodland with bluebells and delicate flowers; summer brings long golden evenings over the lake, and autumn paints the trees in rich, vibrant colours. Step outside to gentle ripples, watch wildlife, or visit East Hoathly village with its café, shop, and pub just minutes away.

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
4.98 out of 5 average rating, 125 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 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, 192 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
Barn in Nutley
4.98 out of 5 average rating, 211 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.

Top Guest favourite
Home in East Sussex
4.84 out of 5 average rating, 153 reviews

Country Home on Ashdown Forest

100th birthday of Winnie the Pooh very close to AA Milne's home & Pooh Bridge. Detached Rustic Arts & Crafts Country House built in 1928 . Spacious bedrooms & 2 extensive reception spaces & large open plan kitchen/diner/breakfast space. Acres of extremely private and tranquil Bluebell woodland & lawns in a peaceful and private wildlife location. Ideal for modest reunions and small groups, quiet getaways, walking, cycling & nearby country pubs. Near vibrant Forest Row & Royal Tunbridge Wells.

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, 293 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
Barn in East Sussex
4.94 out of 5 average rating, 117 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
Shepherd’s hut in Frant
5 out of 5 average rating, 237 reviews

Idyllic Shepherd's hut in a quiet secluded meadow

Cozy inside and with gorgeous views outside, if that sounds like a splendid mix, then set off for the high-weald area of outstanding natural beauty and a self-catering stay at Gabriel's Rest, a gorgeous little shepherd's hut set in a peaceful and tranquil corner of a Sussex meadow with its own little garden. This idyllic retreat is set at Pococksgate Farm. It's all very peaceful here, and a relaxing place to just chill out all by yourselves with no one else around you.

Guest favourite
A shared garden space features a stylish outdoor seating area adorned with colorful cushions. Lush greenery surrounds the area, showcasing a charming wooden building in the background. Open doors invite guests into the interior space, enhancing the connection to the outdoors.
Barn in Friar's Gate
4.97 out of 5 average rating, 218 reviews

The Annex in the beautiful Ashdown Forest

The Annex, a luxury self contained barn studio conversion is located in Ashdown Forest. With a high quality en suite thermostatic power shower, and secure private parking area, The Annex offers an extremely high standard of countryside living. With a luxurious sofa bed, single pull out bed and sumptuous White Company bed linen and towels, there is everything you need to immerse yourself in a calm environment, exuding interior designed soft furnishings.

Top Guest favourite
A clear, geodesic dome reveals a cozy pod interior, surrounded by greenery. An inviting wood-fired hot tub is positioned on a wooden deck, complemented by a dining area. Sunlight illuminates the pod, creating a warm and serene outdoor atmosphere.
Dome in West Horsley
4.94 out of 5 average rating, 395 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Guest favourite
A spacious living area features wooden beams and large windows allowing natural light to fill the room. Comfortable seating includes a patterned sofa and two armchairs. A coffee table holds magazines, complementing the warm wooden flooring.
Cabin in Crowborough
4.95 out of 5 average rating, 411 reviews

“Beautiful and cosy” converted barn

We are offering a beautifully converted barn, in a secluded spot about 150m from our house, at the bottom of the garden. There are two bedrooms and two bathrooms. We are happy to welcome a well-behaved dog. We are in the Wealden Area of Outstanding Natural Beauty, on the edge of the Ashdown Forest - Winnie the Pooh territory - and within easy travelling distance of Tunbridge Wells, Eastbourne, Glyndebourne, Lewes, Brighton and London.

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