Vacation rentals in Five Hundred Acre Wood

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Top-rated vacation rentals in Five Hundred Acre Wood

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Guest favorite

A well-lit bedroom features a spacious bed dressed in soft linens and a dark throw blanket. A contemporary bedside table with a lamp and a small decorative item is positioned beside the bed. Large doors provide access to an outdoor seating area, enhancing the inviting space.

Guest suite in East Sussex

4.91 out of 5 average rating, 232 reviews

One bedroom Annex with private entrance & patio

This listing is a recently refurbished annex attached to the side of the main property. It comes with a private entrance, bathroom, patio outdoor seating area and small kitchenette including a microwave, kettle, toaster and full crockery set. An Air Fryer and Fridge is also available. Tea and coffee is provided with fresh milk and bottled water. Fruit juices are also provided. Only a 5 minute walk to Crowborough town, the location is perfect and also situated on the outskirts of Ashdown forest.

Guest favorite

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, 179 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 favorite

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, 291 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 favorite

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, 268 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 favorite

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, 110 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.

Guest favorite

A charming chalet-inspired studio barn is surrounded by lush greenery, featuring wooden exterior siding and a gently sloped roof. Sunlight filters through the trees, illuminating the inviting entrance and the landscaped garden area in front.

Guesthouse in Buxted

4.95 out of 5 average rating, 828 reviews

Stunning Studio Barn, Buxted

Our chalet-inspired studio barn, with vaulted ceilings and oak beams, is light and airy in the summer and beautifully warm and cosy in the winter, with underfloor heating throughout. It is completely self-contained, with a separate entrance from the adjacent family house. With a sumptuous superking bed (or two twins), sofa bed, unlimited fast WiFi and HDTV, you are assured of a relaxing and welcoming stay in a family-friendly setting in the East Sussex countryside.

Guest favorite

An aerial view of a country house surrounded by lush greenery and rolling hills. The property is nestled within extensive woodland, showcasing a harmonious blend of nature and architecture. Fields stretch into the distance, indicating a tranquil rural setting.

Home in East Sussex

4.84 out of 5 average rating, 146 reviews

Country Home on Ashdown Forest

Detached Rustic Arts & Crafts Country House built in 1928 . Spacious bedrooms & 2 extensive reception spaces & large open plan kitchen/diner/breakfast space. Close to AA Milne's 'Pooh Bridge' (Winnie the Pooh). 2 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.

Guest favorite

Three friendly alpacas are positioned in a lush green field, basking in the sunlight. The animals exhibit varying fur colors: one is black, another is light brown, and the third is white. Surrounding trees and hedges create a natural backdrop.

Cabin in East Sussex

4.89 out of 5 average rating, 483 reviews

The Forest Den

Welcome to The Forest Den which has just been beautifully renovated offering a chic rural retreat. Forest Den is probably the closest accommodation to Pooh sticks bridge and set in the Heart of the Ashdown Forest with direct access into the famous 100 Acre Wood from AA Milne's Winnie the Pooh! Forest Den is a super cosy rural retreat offering a get away from it all lodge at the same time as offering all the creature comforts for a break. New for 2022… Alpacas!

Top guest favorite

A wooden gate made of weathered timber opens to a gravel pathway, bordered by greenery. Beyond, rolling hills and trees are visible under a clear blue sky, creating a serene countryside atmosphere.

Barn in Friars Gate

4.97 out of 5 average rating, 214 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.

Guest favorite

An inviting dining area features a round table surrounded by four white chairs. A decorative bowl is placed at the center of the table. Natural light floods the space through large windows and a skylight, reflecting on the rich wooden flooring.

Cabin in Crowborough

4.95 out of 5 average rating, 382 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.

Top guest favorite

A spacious garden is depicted, featuring well-maintained grass and clusters of vibrant yellow daffodils in bloom. A white building with multiple windows is visible, surrounded by trees and dense shrubs, creating a peaceful outdoor environment.

Apartment in Upper Hartfield

4.93 out of 5 average rating, 136 reviews

Self-contained studio close to Pooh Bridge

Lovely light 1st floor studio flat. Totally self contained with off road parking. Very comfortable king size bed, large living space, kitchen (with fridge & cooker, kettle, toaster), shower/loo and TV. About 500m from both Pooh Bridge as well as an excellent pub. Tea, coffee etc plus welcome pack of cereals, bread, milk and butter will be awaiting your arrival. Use of garden area. Friendly host with equally friendly spaniel.

Top guest favorite

A thatched cottage is seen set against a backdrop of vibrant greenery, beside a tranquil pond adorned with water lilies. The well-manicured lawn features neatly striped grass, enhancing the serene outdoor setting. Sunlight illuminates the scene under a clear blue sky.

Cottage in Rotherfield

4.98 out of 5 average rating, 319 reviews

The Granary at Coes Vineyard, East Sussex

Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.