Holiday houses in Duddleswell

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Top-rated holiday rentals in Duddleswell

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Guest favourite

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

Country Home on Ashdown Forest

(100th birthday of Winnie the Pooh very close to AA Milne's home & Pooh Bridge.) A 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.

ValueFamilyPets

4.84 out of 5 average rating, 159 reviews

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.

Guesthouse in East Sussex

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.

LocationFamilyParking

4.95 out of 5 average rating, 144 reviews

Guest favourite

A spacious country home is nestled among verdant trees and shrubs, framed by an expansive lawn. The structure features a welcoming façade with a sloped roof and large windows, surrounded by lush greenery, creating a serene outdoor setting.

Home in Maresfield

Finches.

Great secluded country get-away destination. Attached annexe with own private entrance. Accommodates 5. Ideal for relaxing weekend. Quiet work space with excellent wifi. Delightful large garden/patio setting overlooking fields. Easy access for car or camper van. Parking in sight of accommodation. Close to many hotel function venues. Sussex National Golf, Glyndebourne, Charleston, Ashdown Forest. Ideally situated for exploring East Sussex. Local mainline station to central London.

ValueFamilyBiking

4.92 out of 5 average rating, 212 reviews

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

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.

FamilyLocationBathroom

4.98 out of 5 average rating, 330 reviews

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

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.

FamilyLocationKitchen

4.92 out of 5 average rating, 304 reviews

Guest favourite

The exterior of a brick building is showcased, featuring two sets of large windows adorned with shutters. A gravel driveway is visible, bordered by flowering plants. The entrance is framed by potted greenery, contributing to a serene and welcoming atmosphere.

Guest suite in Danehill

Country lovers studio with separate access

Hindleap studio is a ground floor bed sitting room with en-suite shower room and kitchenette. Private off-street parking. Located in an Area of Outstanding Natural Beauty, the quiet setting is a short stroll to our local pub which serves great food. With plenty of local walks and visitor attractions nearby such as steam railways, vineyards, national trust properties and quaint villages. Own transport is needed, although the local bus connects to Haywards Heath and East Grinstead.

LocationValueTV

4.93 out of 5 average rating, 322 reviews

Top 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

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.

LocationFamilyHiking

4.95 out of 5 average rating, 130 reviews

Guest favourite

The exterior of a stone barn is depicted, showcasing a sturdy construction with wooden accents. The building features multiple framed windows and a welcoming wooden door. A gravel area surrounds the property, under a clear blue sky.

Guesthouse in East Sussex

Modern barn in the heart of the Ashdown Forest

Our spacious 2 bedroom barn is situated in the heart of the Ashdown Forest and is a perfect base for a walking break. Seek out the locations of Pooh's adventures in AA Milne's books or explore the beautiful South Downs, a short drive away. Our barn is situated within the grounds of our family house. One well behaved dog is allowed. Please be aware we have sheep and other farm animals onsite so dogs must be kept under control at all times. EV charger available at extra cost

ValueLocationHeating

4.86 out of 5 average rating, 267 reviews

Guest favourite

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

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.

LocationValueBreakfast

4.95 out of 5 average rating, 904 reviews

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

The Forest Malthouse | Luxury Barn Retreat

Escape to The Forest Malthouse, a luxurious detached oak-framed barn dating from 1822, beautifully restored and nestled on the edge of the breathtaking Ashdown Forest. Designed exclusively for two, it offers soaring vaulted ceilings, elegant open-plan living and uninterrupted countryside views. Wake to birdsong, explore miles of ancient woodland from your doorstep, then unwind in complete peace and privacy after discovering the very best of Sussex.

LocationFamilyView

4.97 out of 5 average rating, 226 reviews

Top Guest favourite

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

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.

LocationValueBiking

4.9 out of 5 average rating, 554 reviews

Top Guest favourite

The cottage features a traditional two-story design with a charming thatched roof and black timber framing. Lush greenery surrounds the property, while a well-maintained garden showcases colorful flower beds and an expansive lawn, inviting relaxation and outdoor exploration.

Home in East Sussex

Beautiful Countryside Cottage

Perfectly presented picture postcard cottage, on the edge of the Ashdown Forest, the inspiration for the Winnie-The-Pooh books and 3 minutes drive to the historic village of Hartfield for the village store, Pooh Corner tea rooms, pubs and farm shop. This is a great location to explore the Kent & Sussex countryside. The spa town of Royal Tunbridge Wells is a 20 minute drive and only 45 minutes to the South Coast. We are family friendly.

LocationFamilyTV

4.99 out of 5 average rating, 104 reviews