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Holiday rentals in Winchelsea

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Top-rated holiday rentals in Winchelsea

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Top guest favourite
A wooden cottage is framed by well-maintained hedges and greenery. In the foreground, a hot tub is situated on a wooden deck, surrounded by potted plants and shrubs, with clear blue skies overhead adding to the serene atmosphere.
Cottage
4.98 out of 5 average rating, 260 reviews

Blackthorn is a luxurious, rural retreat for two.

Blackthorn is a luxurious retreat for two. Attached to the owner's home, and situated on the edge of Icklesham village, the property lies halfway between the ancient towns of Rye and Hastings. There is a distant view of the sea, and the garden is surrounded by beautiful AONB countryside. The cottage has a private, south facing verandah, and guests are welcome to use the heated, indoor swimming pool and outdoor hot tub throughout their stay but exclusively between the hours of 8.00am and 8.00pm.

Top guest favourite
A serene beach scene features a sandy shore with smooth rocks scattered throughout. The clear blue sky reflects over calm waters, and a cliff with greenery rises majestically in the background, offering a tranquil view of the coastline.
Cottage
4.98 out of 5 average rating, 325 reviews

Pebbles - calm and quiet near the sea

Pebbles is a private annexe at our home in Pett Level, a haven of quiet and calmness. You’ll be only five minutes walk from an amazing beach. Surrounded by fabulous countryside and cliff top walks, 2 local pubs in the village of Pett, 5 minutes car ride or a lovely 1/2 hour walk away over the hills. There is a bright lounge with french doors overlooking the garden, wet room, double bedroom and fully fitted kitchen. The garden is secluded and peaceful . The beautiful town of Rye is 5 miles away.

Guest favourite
A cozy sitting area features a green sofa positioned beside a colorful area rug. A log burning stove with a decorative mantel stands prominently, while a bright yellow kitchen area offers essential amenities. Natural light filters through the window, creating an inviting atmosphere.
Cottage
4.9 out of 5 average rating, 184 reviews

Peace, Quiet, Cosy house with garden & log burner

Peaceful, with good views, great walks, 2 sitting rooms, big cosy log burning stove, big fluffy towels & dressing gowns, 600TC sheets, super comfy bed, plumped pillows, 2 big smart TVs, wifi & Sonos. Soak in a free-standing bath or big shower and stretch out on an enormous sofa and admire the view up the valley - You won't want to leave! If you do the Little House is well placed for pubs, beaches, vineyards, gardens, Rye and Hastings and many other treats only a walk or short drive away.

Top guest favourite
A charming outdoor seating area features a light blue table and two matching chairs placed on a gravel surface. Surrounded by greenery and colorful flowers, the entrance to the cozy cottage is visible in the background, framed by a wooden trellis overhead.
Cottage
4.95 out of 5 average rating, 113 reviews

Delightful 2 bedroom hideaway close to beach

Woodview is ideal for a romantic get away by the sea or a bird-watching holiday on the wonderful Rye Harbour Nature Reserve. This cosy cottage has free parking on site and lots of secluded outdoor space with a range of seating and dining areas. Recently refurbished throughout, it has a well-equipped new kitchen and shower room. Winchelsea Beach Village has good amenities and is close to a wide range of local historic and countryside attractions that can be enjoyed all year round.

Guest favourite
Barn
4.94 out of 5 average rating, 211 reviews

Tillingham View near Rye

A converted steam engine house, Tilingham View has far reaching views of open countryside, the Tillingham Valley and beyond to Rye. Benefitting from a woodburning stove and mezzanine bedroom with a window overlooking the wonderful view. A very pretty garden is shared with the owner. One well behaved dog welcome. There is a fully equipped kitchen with microwave, electric oven and hob. In the lounge is a Smart TV with full TV package and BT Sport.

Guest favourite
The open-plan living area includes a light-colored sofa and armchair, accompanied by a white coffee table. A television is situated on a stand, while large windows with blue curtains allow natural light to illuminate the space.
Cottage
4.82 out of 5 average rating, 328 reviews

The Stable Cottage on beautiful farm

The Stable Cottage is a delightful one bedroom cottage overlooking The Brede Valley to Winchelsea and the sea. Set on a working arable and sheep farm. Adjacent to the Woolroom Cottage and a term time only Nursery. Guests can enjoy lots of walks on the farm, plentiful bird life, including barn owls. The property is close to the historic town of Rye, Camber sands beach, Winchelsea beach, Battle Abbey and Bodiam Castle.

Top guest favourite
A spacious sleeping area features a comfortable bed dressed in light linens and a bright yellow blanket. The decor includes soft pillows and artwork decorates the walls. A kitchenette is visible in the background, along with a small dining area bathed in natural light from the skylight above.
Flat
4.94 out of 5 average rating, 191 reviews

Cosy Fairlight Studio Flat

Our cosy studio apartment is in a quiet private Cul-De-Sac. We are within walking distance of the beautiful cliff top walks of the Hastings Country Park and Firehills with its spectacular views across the Sussex coast. Hastings old town, the medieval town of Rye and historic Battle are a short drive away. The property is surrounded by trees and hedgerows and there is a secluded front garden to eat outside in the summer.

Top guest favourite
An open plan living area is presented with a cozy seating arrangement, featuring a comfortable armchair and a vintage trunk coffee table. A dining area with a round table and white chairs is visible, along with a decorative fireplace and a cheerful bouquet of flowers.
Flat
4.94 out of 5 average rating, 261 reviews

Hamilton Nest

Romantic holiday apartment centrally located in the medieval town of Rye Stylishly decorated throughout to offer comfortable accommodation Within walking distance of Rye’s independent shops, cafes and restaurants Close to Camber Sands beach, Rye Harbour Nature Reserve, Tenterden and Hastings Visit the historic houses, gardens and vineyards the area has to offer Great for walkers with easy access to local footpaths

Top guest favourite
A charming bedroom is highlighted by a striped headboard adorned with decorative pillows. An accented wall in warm tones complements framed artwork above the bed. A small tray table holds a vase with fresh flowers, adding a touch of color and elegance to the space.
Home
4.98 out of 5 average rating, 123 reviews

The Yard Rye

The Yard is a two-bed interior-designed cottage in the citadel of the beautiful Cinque Port town of Rye. It is situated down a cobbled passageway next to a pretty tea room. PLEASE NOTE – The property can sleep up to two adults in the master bedroom and one child in the single, with a pull-out camp bed if needed for an extra child. We also have a travel cot for an infant. Please be aware we have a steep staircase.

Top guest favourite
An outdoor space is featured, showcasing a hot tub surrounded by lush greenery and vibrant flowers. A circular dining table with wooden chairs is positioned nearby, complemented by additional seating for relaxation. Sunlight illuminates the area, enhancing the natural beauty of the garden.
Holiday home
4.99 out of 5 average rating, 384 reviews

Sea View Holiday Flat + Pool & Spa in Countryside

Luxury studio flat with a spectacular view of the sea and countryside. New: Large private balcony to sunbathe and dine outside. Heated indoor swimming pool, steam room, gym, and outdoor hot tub. King size bed with en-suite, suitable for 2 people. Free high speed wifi throughout. Large smart TV with 200 satellite channels and free Netflix. Located in Hastings Country Park Nature Reserve, short walk to beach.

Top guest favourite
A stylish lounge bedroom features a king size bed adorned with a floral patterned duvet and plush pillows. A navy throw blanket is neatly placed at the foot of the bed. The room's walls are painted in a deep blue, and a wall clock is visible.
Apartment
4.96 out of 5 average rating, 401 reviews

Beautiful boutique studio flat in town centre

Enjoy a stylish experience at this centrally-located place. This newly finished studio flat with fully furnished kitchen and dining area is in the centre of Medieval Rye, making it the perfect base to explore the historic Sussex south coast. This is a new property for us, however we are established hosts with super host status. Please do message if you have any questions. We’d love to hear from you.

Guest favourite
A well-equipped kitchen features open shelving displaying dishes and cookware. Light wood flooring extends into a cozy living area with large glass doors opening to a garden. A dining table is positioned nearby, enhancing the space's functionality and warmth.
Bungalow
4.9 out of 5 average rating, 441 reviews

Kahytten Beach House on Winchelsea Beach

Kahytten [Danish for ships cabin but also used to describe a fisherman’s retreat] is a cosy and light filled beach house, two minute's walk from the beach in a lovely seaside village with good amenities. Ideal for couple or small family. Well equipped kitchen, central heating and cosy living space. This is a lovely space all year round with beautiful walks on beach and nature reserve.

Popular amenities for Winchelsea holiday rentals

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  2. United Kingdom
  3. England
  4. East Sussex
  5. Winchelsea