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 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, 122 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 modern cabin, constructed from wood, is illuminated by warm light against a nighttime backdrop of trees. A circular wood-burning hot tub, glowing with turquoise water, is positioned in the foreground, inviting a peaceful outdoor experience.
Shipping container in Whitesmith
4.97 out of 5 average rating, 119 reviews

Unique shipping container cabin in private woods

AS SEEN ON TV ! George Clarkes Amazing Spaces Season 12 episode 1. Evergreen cabin is set in it's own private woodland in the heart of the East Sussex Countryside. The Cabin is a two story shipping container home with enormous picture windows bringing the outside in. A free cooking fire pit in the woods. Hampers are avalable as optional extras. The book "playing it by ear" is avalable at all good independent bookshops. The optional extra of a wood burning hottub **(£85 with bag of logs)**

Guest favourite
An open-plan living area is visible, featuring a contemporary glass dining table with four chairs. Sliding patio doors lead to an outdoor terrace, framed by sunlight and natural views. The room displays a cozy seating area with a sofa and decorative artwork on the walls.
Cottage in East Sussex
4.95 out of 5 average rating, 119 reviews

Stylish Cottage, Glorious views, 4* Gold rated

Rated 4* Gold by Visit England. Rural retreat 1 hour from London. Modern detached cottage with private garden set in 4 acres of pasture & woods. Enjoy glorious views from both from inside and from patio and decking platform. Access to heath & bird hide overlooking 450 acre RSPB nature reserve. Woodburner & luxury underfloor heating throughout. 2 ensuite bedrooms with TV's, king & super king beds, living/dining area with 43" smart TV. 1.5 miles from Regency spa town of Royal Tunbridge Wells.

Guest favourite
Guest house in East Hoathly
4.94 out of 5 average rating, 154 reviews

‘The Water Snug’ Beautiful Floating Cabin

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
4.97 out of 5 average rating, 104 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
Shepherd’s hut in Rotherfield
4.98 out of 5 average rating, 257 reviews

Pigeon Hole, Organic Vineyard stay with Pool.

Woodland Shepherds Hut situated at Coes Farm an Organic Vineyard and Orchard making Natural wines and cider, 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. We planted our 5 acre organic vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Top guest favourite
Place to stay in Wadhurst
4.99 out of 5 average rating, 600 reviews

Luxury architectural retreat/ East Sussex views

Oliveswood barn a self contained contemporary Architect designed Barn is a luxurious couples retreat, a detached structure surrounded by beautiful AONB countryside with outstanding views. Dog friendly. Close to many famous houses and gardens ,Sissinghurst Castle, Great Dixter, Chartwell, Batemans and Scotney Castle. The Spa town of Royal Tunbridge Wells is a 20 minute drive away. Wadhurst our nearest village has 2 small supermarkets, great butcher, deli, 2 pubs and takeaways.

Top guest favourite
A stone patio is presented with a rectangular table surrounded by two woven chairs. Bright red and white flowers are arranged in planters along the patio's edge, with greenery accentuating the space. A brick wall provides background structure, while large glass doors offer access to the interior.
Barn in Ripe
5 out of 5 average rating, 116 reviews

Country barn with beautiful views

Exclusive use of spacious fully-equipped barn with beautiful views of the South Downs National Park. Set in a quiet, rural location within walking distance of the historic village of Ripe, near Lewes, East Sussex. An ideal location for country walks and cycling with local restaurants and pubs nearby. Within easy reach of the coast, the towns of Lewes, Brighton and Eastbourne, Glyndebourne Opera House, Michelham Priory, and many other places of historic interest.

Guest favourite
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 Friar's Gate
4.97 out of 5 average rating, 215 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 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.
Flat in Upper Hartfield
4.94 out of 5 average rating, 146 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 favourite
The exterior of The Old Cart Shed is shown, featuring a traditional wooden structure with a distinctive dark wood facade and a sloped red roof. A bright wooden door is visible, surrounded by a neatly manicured lawn and young shrubs along the pathway.
Barn in Lindfield
4.99 out of 5 average rating, 118 reviews

Luxurious hideaway in an area of natural beauty

‘The Old Cart Shed’ is, as the name contrives, a property fabricated from the structure of an original 19th century cart shed. Rebuilt entirely from the ground up, with only the interior, original wood-beamed structure and lime render walls to belie any relation to its former purpose, The Old Cart Shed is today, a self-contained, redesigned dwelling available for short or long-term rental.

Popular amenities for Five Hundred Acre Wood holiday rentals