Holiday rentals in North Chailey

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Top-rated holiday rentals in North Chailey

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Top guest favourite
An outdoor hot tub is situated on a wooden deck, surrounded by lush greenery. A seating area with a light-colored chair offers a comfortable spot to relax. Large sliding glass doors lead into the retreat, allowing for seamless indoor-outdoor access.
Shepherd’s hut in Chessington
4.99 out of 5 average rating, 193 reviews

Lavish Retreat & Champagne 30mins Taxi from London

The Little Touch of Grey, provides an electric ambiance and the perfect setting for the elite of mind, who wants to reward both themselves and their partner. We are proud to share the latest addition to our portfolio with those who appreciate of all things bespoke. Included are; a complimentary bottle of Champagne, indoor & outdoor Jacuzzi, underfloor heating, sound system and salacious yet tasteful surprises throughout. For special occasions, use our secret compartment to add to your surprise.

Guest favourite
A charming treehouse, built from cedar wood, is nestled among lush greenery. The structure features a conical roof and large, arched windows. A wooden boardwalk with steps leads to the entrance, surrounded by vibrant leaves and natural scenery.
Treehouse in Mayfield
4.99 out of 5 average rating, 144 reviews

Luxurious, picture-perfect, stunning treehouse

Hoots Treehouse is a picture-perfect, romantic, luxurious treehouse with all mod cons in an area of outstanding natural beauty - only 45 minutes south of M25. Clad in aromatic cedar wood, beautifully furnished - ideal private, woodland retreat for couples. Can also comfortably sleep up to 2 children (from 5 years) on single mattresses in loft area accessed by a ladder and hatch. NOT SUITABLE FOR 4 ADULTS. A wonderful place to chill-out and lose yourself - you won't want to leave! Sheer bliss!

Top guest favourite
A quaint outdoor seating area is surrounded by lush greenery, featuring four wooden chairs arranged around a stone table. Flower pots and a log storage are visible against the brick wall, with the main entrance partially obscured by climbing vines.
Home in North Chailey
4.92 out of 5 average rating, 143 reviews

self-contained 2-bed home in Sussex countryside

The annexe is adjacent to the main house and a perfect country getaway suitable for a quiet holiday, visiting local Sussex attractions, or a handy base for visiting friends or family. The house itself is late Victorian, with generously proportioned rooms and high ceilings. There are 2 interconnecting bedrooms with a shared shower room. Both bedrooms have double beds. Breakfast isn't provided but there is a kitchen for self catering. The living area has a woodburning stove. NB there is no tv!

Top guest favourite
Guest house in East Hoathly
4.93 out of 5 average rating, 192 reviews

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 every room. 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
Guest house in Haywards Heath
4.94 out of 5 average rating, 229 reviews

Romantic retreat

Spa with hot tub and sauna all heated via a log burner for the ultimate retreat break. Guest house in large gardens, king sized bed, small kitchen and en-suite. Many local attractions near Brighton Gatwick Airport and the South Downs! Pull out double sofa bed, works well for smaller family’s. Stunning 25 meter swimming pond, water is crystal clear. Large deck and sun-loungers by the swimming pond. We use the garden too, it’s part of our home but there is plenty of opportunity for privacy.

Top guest favourite
A wooden container is set on a sunlit deck, surrounded by a grassy area and fenced on the sides. A small table and chairs are positioned near the entrance, while an L-shaped sofa is located on the deck. The backdrop features a green field and trees.
Shipping container in East Chiltington
4.98 out of 5 average rating, 307 reviews

Modern 1 bed, converted shipping container.

Enjoy a stay in the heart of the South Downs surrounded by nature. Whether you want a break away from the rush of everyday life, or a peaceful place to work from. Our cosy container is a beautiful sun trap, attached to our family racing yard. You’re in the perfect location for business or pleasure. footpaths a short walk away. The bottom of the downs a five minute drive and a handful of pubs all within a 5mile radius. Plumpton station a 2 minute drive you can be in London within the hour.

Guest favourite
A quaint shepherd's hut features light green exterior walls and a gently curved roof. A small wooden porch with two steps leads to the entrance. Outdoor seating is positioned nearby, showcasing a table and two chairs surrounded by lush greenery.
Shepherd’s hut in Plumpton
4.88 out of 5 average rating, 217 reviews

Comfy and cosy hut in stunning private location

The shepherd's hut is located in a private and peaceful spot on our smallholding, on the outskirts of the South Downs National Park. The hut has great amenities and is heated. It has great access to footpaths and local shops and pubs. We are fortunate enough to have some wonderful wildlife here, including deer, birds of prey and woodpeckers. As well as our rare breed sheep and pigs. Issy is a land agent and Geoff is a tree surgeon, so we have a keen interest in nature and the environment.

Guest favourite
A spacious barn-style home is showcased against a clear sky, featuring a stone façade and large windows. A grassy lawn extends in front, with shadows cast by trees. Outdoor seating is positioned on a patio area, and a swing set is visible in the background.
Barn in Milton Street
4.94 out of 5 average rating, 211 reviews

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.

Top guest favourite
A tractor is seen working in a sunlit field, surrounded by trees. The warm light of early morning creates a gentle glow, highlighting the lush greenery nearby. The stone wall in the foreground frames the serene rural landscape.
Cottage in Wivelsfield Green
4.96 out of 5 average rating, 171 reviews

Green Park Farm Barn

In the heart of Mid-Sussex, our former dairy farm dates back to the early 1800's. The barn has been recently restored to provide 1000 sq ft of luxurious accommodation with wonderful views across the wheat fields to the west. Guests can enjoy countless walking and cycling trails from the front door. Brighton, historic Lewes, Glyndebourne, Hickstead and the South Downs are all a stones throw away. Gatwick is less than 30 mins by car and London a further 45 by train.

Top guest favourite
A charming black cottage sits beside a tranquil pond, framed by trees showing autumn colors. Large windows reflect the natural surroundings. A green bench invites relaxation on the grassy area, with a rainbow arching over the scene, enhancing the peaceful rural landscape.
Farm stay in Barcombe
4.98 out of 5 average rating, 100 reviews

The Bull Pen

Set in a peaceful farm location, The Bull Pen is on the edge of the wood, overlooking the pond. It is recently converted, upcycling wherever possible. The farm includes award-winning ancient woodland run as a nature reserve - great for a quiet weekend away, or a longer rural retreat. Highlights include butterflies, bluebells and nightingales in season. The village of Barcombe is within walking distance and Lewes and the South Downs are a short drive away.

Guest favourite
A wooden lodge with a contemporary design is set beside a serene lake. Decking extends from the structure, providing outdoor space overlooking the water. Surrounding greenery includes various trees, enhancing the natural atmosphere of the location.
Home in North Chailey
4.86 out of 5 average rating, 159 reviews

Lakeside Retreat- The Boat House

The Lakeside Retreat is a self-contained lodge on the edge of a lake boasting complete privacy, in the heart of a working farm in the picturesque county of Sussex. The cabin benefits from an open plan living and kitchen area with floor to ceiling glass doors that open out onto decking. Relish an escape from modern-day life surrounded by uninterrupted farmland. Find us on social media @thelakesideretreatsussex or online by searching for lakeside retreat.

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, 362 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.

Popular amenities for North Chailey holiday rentals

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