Holiday rentals in Wilsley Pound

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Top-rated holiday rentals in Wilsley Pound

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Top guest favourite
A charming shepherd's hut is positioned amidst vibrant flowering shrubs, featuring a welcoming entrance with steps. A cozy seating area, including a table and chairs, is placed nearby, complemented by a firepit in the foreground that enhances the outdoor space.
Shepherd’s hut in Cranbrook
4.96 out of 5 average rating, 127 reviews

Spacious luxury shepherds hut with woodburner

The Sheepcote, our brand new spacious shepherds hut, is based in the Kent High Weald Area of Outstanding Natural Beauty. It sits in its own south facing half acre garden with fruit trees, silver birch and a young oak tree. Outside there’s plenty of parking and an area with a bench, table and chairs where you can relax and enjoy the countryside, watch the buzzards fly overhead and in the evenings listen out for the soft hooting of our resident owls! Its the perfect place for a romantic break.

Guest favourite
A spacious bedroom features a comfortable kingsize bed with soft linens and decorative pillows. A lamp provides gentle lighting, while neatly hung bathrobes await nearby. Framed artwork adorns the walls, contributing to a serene atmosphere.
Cabin in Benenden
4.97 out of 5 average rating, 242 reviews

The Summer House Benenden (near Sissinghurst) Kent

Attractive comfortable charming private annexe in the garden of the owner's home. Quiet residential area in Benenden village. Spacious airy accommodation consists of large room with kingsize bed with luxurious cotton bedlinen, a table and chairs, kitchen trolley with fridge kettle toaster. Breakfast : artisan bread preserves apple juice milk from village dairy granola and fresh fruit. Ensuite shower room. Bathrobes. Private courtyard garden. Smart TV Wifi. Iron available on request

Top guest favourite
A restful bedroom features a super kingsize bed with white linens and textured pillows. Complementing nightstands with lamps are positioned on either side. A round mirror and artwork enhance the tranquil atmosphere, while soft light illuminates the soothing green walls.
Cottage in Benenden
4.97 out of 5 average rating, 173 reviews

Old Fire Station in central Benenden village, Kent

Nestling in the idyllic Weald of Kent countryside, the Old Fire Station is the perfect place for a relaxing stay in the centre of historic Benenden village. The spacious, self-contained accommodation sleeps four, with a separate bedroom with super kingsize bed and sitting room with two single sofa beds. The listed former village fire station is within walking distance of The Oak Barn wedding venue and Benenden School, or a short drive to Benenden Hospital and the gardens of Sissinghurst Castle.

Top guest favourite
A small wooden cabin is set against a backdrop of lush greenery and a clear blue sky. Several sheep graze peacefully in the vibrant green grass surrounding the cabin, with a wooden fence delineating the area.
Farm stay in Biddenden,Ashford
4.97 out of 5 average rating, 339 reviews

Ayleswade shepherd hut in Kent countyside

set in the small village of biddenden in the heart of the kent countryside belonging to a local farming family of many generations .You can expect beautiful country walks with many footpaths and local villages nearby for cream teas and lovely lunches , the nearby village of Headcorn with its straight connections to London or the coast is good for sightseeing, you wake up to views of our sheep and free range chicken and enjoy a relaxing cup of tea.Theres milk ,tea and coffee and our eggs for you

Guest favourite
The Garden Studio is presented with large floor-to-ceiling windows featuring soft curtains. A wooden deck is adorned with a seating area, surrounded by manicured grass and flowering plants, offering a serene outdoor space for relaxation.
Guest house in Sissinghurst
4.93 out of 5 average rating, 193 reviews

Self Contained Garden Studio with stunning views

The Garden Studio has spectacular views over the Kent countryside from the property's floor to ceiling windows. The self contained compact studio has private access and includes lounge chairs, coffee table and a double bed. We have a dining table/ two stools overlooking the terrace. There is a fridge, a microwave, a two ring electric hob together with a kettle, Nespresso Coffee Machine and a toaster in the kitchen area. Iron/Board/Desk/Chair are on request prior to stay. Compact shower/wc.

Guest favourite
A charming brick exterior showcases a green door complemented by a lattice screen and a blossoming plant nearby. The towering Victorian chimney rises prominently against a clear blue sky, highlighting the unique character of the converted building.
Tiny home in Frittenden
4.89 out of 5 average rating, 154 reviews

Tiny Rural Chimney House

Enjoy the lovely setting of this romantic spot in rural Kent. The Tiny Chimney house boasts stunning countryside views and fantastic walks. Step out the door and follow public footpaths directly to Sissinghurst castle, local woods or some fabulous local pubs. Located in a conservation area The Tiny Chimney house is a converted brick building attached to a quirky 40ft Victorian Chimney. The room sleeps two and is ideal for hikers or a couple's rural escape, but still within an hour of London.

Guest favourite
A large glass sliding door showcases expansive views of the surrounding countryside. The open-plan living area features a comfortable seating arrangement and a small table, inviting relaxation and connection with nature. A patio area with outdoor furniture is visible beyond the glass.
Guest house in Iden Green
4.94 out of 5 average rating, 123 reviews

Contemporary rural retreat with breathtaking views

The Rookery is a well located private space with stunning South-facing views across an Area of Outstanding Natural Beauty. An ideal base to explore countryside & coast, ancient forests & villages, historic castles, famous beaches and cosy local pubs. Just 15 min to Sissinghurst Castle & garden, Bodiam & Scotney Castle, 20 min to Rye & 30 min to the dunes & beach at Camber. Explore local walks, Go Ape at Bedgebury Forest, paddleboarding & watersports or tour our local wineries.

Top guest favourite
A charming black timber cottage is surrounded by lush greenery and neatly trimmed hedges. A well-maintained lawn extends in the foreground, leading to a wooden fence that provides a sense of privacy while natural light enhances the serene landscape.
Guest house in Biddenden
4.96 out of 5 average rating, 151 reviews

Little Batchelors - Idyllic escape

Set in the grounds of a stunning 400 year old Tudor Hall and gardens, this beautiful new property is 1.5 miles away from the gorgeous Sissinghurst Castle Garden and within easy reach of Biddenden, with its renowned vineyard and Michelin starred restaurant. A perfect setting for couples, small families or friends. It has a very large open plan living/dining/kitchen area with doors onto a decked terrace and two en-suite double bedrooms, with ample room for parking.

Guest favourite
A covered outdoor area is illuminated by string lights, showcasing a large table and various seating options. Two comfortable lounge chairs are accentuated by a patterned rug. Lush greenery surrounds the space, creating an inviting atmosphere for gatherings or relaxation.
Cottage in Sissinghurst
4.92 out of 5 average rating, 219 reviews

Walk to Sissinghurst Castle. Covered heated patio

The Outside Inn is a newly renovated 19th Century weatherboard barn. It has an open plan kitchen/dining/living area. There is 1 large bedroom with a Super King bed There is 1 bathroom with a large walk in powerful shower. The kitchen is fully equipped with oven, dishwasher, coffee machine etc. The sitting area has a very comfortable sofa. There’s a 9m x 4m covered outside area - bbq, dining, rocking chairs, and heaters to make it useable all year round

Top guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 871 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Top guest favourite
Cottage in Sissinghurst
4.98 out of 5 average rating, 180 reviews

Peaceful Cottage with Views nr Sissinghurst Castle

Weaver's Rest offers peace and tranquility in the garden of England within easy reach of beautiful walks, English Heritage sites, and medieval villages. This well-equipped cottage is situated in the stunning High Weald Area of Outstanding Natural Beauty. Local pubs, shops & restaurants are within walking distance or enjoy your own meals gazing over surrounding countryside at home. The hosts live next-door.

Top guest favourite
A modern kitchen is showcased with navy cabinetry and a light countertop. Appliances, including an electric oven and fridge, are neatly arranged. A breakfast bar with high stools complements the open layout. Natural light fills the space from a window, illuminating the grey tiled floor.
Home in Saint Michaels
4.96 out of 5 average rating, 116 reviews

Guest house in St Michaels

Take a break and unwind at this peaceful residence with beautiful views and modern stylish interior with secluded patio. Located a short drive from the historic picturesque town of Tenterden with its restaurants, pubs, shops and the Kent and Sussex steam railway. Chapel Down and Biddenden vineyards are both a short drive away as well as forests, gardens, castles and national trust properties.

Popular amenities for Wilsley Pound holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Kent
  5. Wilsley Pound