Holiday houses in Crowborough

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Top-rated holiday rentals in Crowborough

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Top Guest favourite
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, 252 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.

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, 105 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 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, 183 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.

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, 278 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.

Top Guest favourite
A spacious living area is highlighted by large windows offering views of the surrounding greenery. A comfortable sofa and an ottoman complement a soft area rug. A television and a small lamp add functionality, while houseplants contribute to the relaxed ambiance.
Condo in Blackboys Near Uckfield East Sussex
4.98 out of 5 average rating, 166 reviews

Peaceful spacious country barn with amazing views

Gunbanks Forge TN225HS is in the heart of the Sussex countryside amongst the grounds of Gunbanks Farm. It is a peaceful retreat to escape the stress of daily living. Tucked away down a private drive with easy parking. There is an outside space to sit and relax. The barn is spacious and sociable. There is a working forge just by the barn. Occasionally there will be farriers making shoes and wrought iron pieces. You will see evidence of this around the garden with beautiful balls.

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
4.94 out of 5 average rating, 111 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 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
4.95 out of 5 average rating, 840 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 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.

Guest favourite
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, 389 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 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.
Apartment in Upper Hartfield
4.94 out of 5 average rating, 143 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
A charming thatched cottage is surrounded by meticulously maintained gardens featuring geometric hedges and a stone pathway. Lush greenery and trees frame the scene, while a tranquil pond reflects the clear sky above.
Cottage in Rotherfield
4.98 out of 5 average rating, 336 reviews

The Granary, Organic Vineyard stay with Pool.

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.

Top Guest favourite
The exterior of a single-story annex features a warm wooden front door framed by rows of windows. Brickwork complements the natural landscaping, which includes flowering shrubs and a variety of greenery. A small bench sits beside the entrance, inviting relaxation.
Guest suite in Langton Green
4.95 out of 5 average rating, 389 reviews

Little Stonewall’s Guest Suite

A newly refurbished self-contained annex in the heart of Langton Green. Available for short stays and longer lets (1 / 2 / 3 months). Village green and popular countryside pub a mere 400 metres away, this is an ideal location for a countryside getaway. And with Royal Tunbridge Wells’ shops and restaurants 2.5 miles away, you really will be able to experience the best the area has to offer. Parking available on site.

Popular amenities for Crowborough holiday rentals

When is the best time to visit Crowborough?

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Frequently Asked Questions

  • Where should I stay in Crowborough?

    Make yourself at home in Crowborough by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Boarshead, and over 50 vacation rentals in Poundgate.

  • Are there vacation rentals with a dedicated workspace in Crowborough?

    Yes! Work meets play with ease at over 10 vacation rentals in Crowborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Crowborough?

    Four-legged friends are welcome in Crowborough. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Crowborough?

    Crowborough has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Crowborough

  • Total holiday rentals

    Explore 20 holiday rentals in Crowborough

  • Nightly prices starting at

    Crowborough holiday rentals start at $90 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Crowborough holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Crowborough rentals

  • 4.9 Average rating

    Crowborough stays are highly rated by guests—averaging 4.9 out of 5!

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