
Holiday houses in Five Hundred Acre Wood
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Top-rated holiday rentals in Five Hundred Acre Wood
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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.

Seaview Stay
Seaview Stay is cliff top escape with uninterrupted panoramic sea views. Enjoy the wonderful sunset and sunrise in this comfortable stylish 1 bedroom annex with your own terrace and private access. We are a 15 minute drive or a short bus ride into Brighton town centre with the added bonus of a beautiful and quiet location to return home to. Directly on the East Sussex coastal path with the nearest beach access only 5 minutes walk, also a short stroll into the beautiful South Downs National Park.

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.

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.

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.

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.

Idyllic and Secluded Lakeside Lodge
Reconnect with nature at this unforgettable escape. Taylor’s Lodge is set in beautiful surroundings overlooking a private lake. We have ducks, chickens, two cats and a friendly dog. Enjoy feeding the fish, you might even see the heron on his daily visit! No fishing please. We are set in 4 acres with beautiful walks to Buxted Park, Ashdown Forest. There are two pubs within a short walk, both excellent food. Our lodge is fitted out to provide a comfortable stay with nature in abundance.

Cosy, Rustic 17th Century Country Barn.
Charming 17th century Barn conversion. Restored with every attention to detail, abundance of character & exposed beams, fully equipped kitchen, attractive bathroom with roll top bath & rain shower. Underfloor heating, High Speed Wifi, Smart TV and optional hot tub (please enquire and book in advance). Just 14 minutes from Gatwick Airport/Station & the Express into London takes only 30 minutes, yet the Barn is set in open countryside, surrounded by fields, on an Equestrian property

Beautiful barn on the South Downs Way
Beautiful barn, perfect for walkers, also great as a comfortable and spacious base for exploring the local countryside. Local cultural attractions include Glyndebourne, Drusilla's Park, South Downs Way. This spacious artist's home is located right on the South Downs Way, and it is only about an hour and a half walk to the coast at Exceat. There is a tree house for kids, a couple of swing seats for chilling out on, and the Cuckmere runs through the bottom of the garden.

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.

Re-furbished former dairy, 100 yards gastro pub
The recently renovated Old Dairy is a modern standard, cosy, compact space, set within a medieval farmstead in the quiet village of High Hurstwood. The Old Dairy is just 100 yards walk from the popular Hurstwood gastro pub. Enjoy the tranquility and local walks or a short drive to Tunbridge Wells, Eastbourne, Lewes, Brighton, the Ashdown Forest, the South Downs. The Old Dairy has a vaulted living space with a king sized bed, sleeping 2 on a mezzanine level.

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.
Popular amenities for Five Hundred Acre Wood holiday rentals
Other great holiday rentals in Five Hundred Acre Wood

Self contained chalet annexe -Adults only-

Cosy small cottage

Beautiful Countryside Cottage

Self-contained studio close to Pooh Bridge

Pelsham Farm Bungalow

A luxurious country retreat with Jacuzzi hot tub

The Barn, Hot tub, projector, Fire Pit, Pizza oven

Entire converted stone coach house
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- ExCeL London
- The O2
- Brighton Seafront
- Tower Bridge
- Emirates Stadium
- West Wittering Beach
- Clapham Common
- Goodwood Motor Circuit
- South Downs National Park
- Buckingham Palace
- Thorpe Park Resort
- Alexandra Palace
- Chessington World of Adventures Resort
- Big Ben
- London Stadium
- Windsor Castle
- LEGOLAND® Windsor Resort





