Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

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Top guest favorite

Cottage

4.98 out of 5 average rating, 245 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 favorite

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

4.97 out of 5 average rating, 310 reviews

Pebbles - calming 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.

Top guest favorite

A spacious living area features large windows that frame captivating sea views. A wooden dining table is set between the windows, accompanied by two chairs. A plant is placed on each side of the room, and simple furnishings are styled for a relaxed atmosphere.

Apartment

4.99 out of 5 average rating, 109 reviews

Escape to the Sea

Gorgeous, spacious, south-facing flat with stunning sea views, original features, and high ceilings. The sunrises/sets and moon reflections are breathtaking! In between St Leonards on Sea and Hastings, and 30 seconds to the beach! The bedroom has a king size bed and the living room a double sofabed. Bedding is cotton/linen washed with non toxic products. Flat is on the 3rd floor but not that many stairs and as such, sea views far from the madding crowd! There is free parking nearby

Top guest favorite

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, 111 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.

Top guest favorite

A cobbled street lined with traditional timber-framed houses showcases the architectural charm of the area. The buildings feature decorative leaded glass windows and steep roofs, with greenery and street lamps adding to the historic ambiance. A clear sky can be seen above.

Home

4.98 out of 5 average rating, 187 reviews

Unique 14th century house in the Citadel of Rye

Hucksteps is a medieval, 3 bedroom/2 bathroom house centrally located in the Citadel of Rye. Facing St Mary’s Church, the house is surrounded by cobbled streets, period architecture, literary associations, stunning coastline, and vibrant culture. Camber's sandy beaches and dunes are an easy walk/cycle/drive away. A High Street full of independent shops, restaurants, inns, art galleries, Kino cinema, Rye Spa Retreat, tea rooms is round the cobbly corner.

Guest favorite

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, 311 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 favorite

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.

Apartment

4.94 out of 5 average rating, 185 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.

Guest favorite

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.

Apartment

4.94 out of 5 average rating, 250 reviews

Hamiltons 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 favorite

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.

Condo

4.95 out of 5 average rating, 371 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.

Superhost

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, 423 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.

Guest favorite

Cottage

4.97 out of 5 average rating, 270 reviews

Perfect Isolation. Quaint Sussex Farm Cottage

Refurbished Spring ‘22 The perfect rural bolthole. Think The Holiday but you will need to supply Jude Law & Cameron Diaz. Waggoners is a private & quaint, cottage set in idyllic isolation, on a working farm, with luxurious handpicked furnishings. Outside- you are spoilt with a patio that bathes in sunshine all day. Please also see my other listings for further availability

Top guest favorite

A detached cottage is showcased with a well-maintained garden and a wooden deck. A rose bush climbs the trellis at the forefront, while an open grassy space extends to the back, framed by rustic fencing and trees in the background.

Guest suite

5 out of 5 average rating, 204 reviews

Valley View Cottage

We would like to welcome you to our detached cottage in the small village of Icklesham, between Hastings and Rye. With open countryside on the doorstep, there are plentiful walks including the 1066 Country Walk which runs long side the property. With comfortable space both inside and out, you can also just take it easy and enjoy the peace and tranquillity on offer.