Cottage vacation rentals in Winchelsea

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Top-rated cottage rentals in Winchelsea

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Guest favorite

A wide view of Pett Level Beach shows a stretch of sandy shoreline under a partly cloudy sky. Gentle waves lap at the shore, while a shallow pool reflects the sky. Several beach huts are positioned along the distant coastline.

Cottage in Pett Level

4.93 out of 5 average rating, 167 reviews

Lovely Unique Beachfront Cottage

Stay right on wonderful Pett Level Beach in one of the original Coastguard's cottages, with direct access from the garden straight onto the sand. Recently modernised, the cottage has a super stylish open plan ground floor with kitchen, dining and living areas and wood burning stove. Upstairs there are two bedrooms: one has a double bed and sea view, the other can be made up either as a kingsize or as two single beds. Flexible space perfect for families or friends. A rare, stunning property.

Top guest favorite

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 in Icklesham

4.98 out of 5 average rating, 243 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

The cabin showcases a wooden exterior with a welcoming deck, furnished with outdoor chairs. Surrounding greenery adds to the serene setting, while a gently sloped area leads up to the entrance, framed by a rustic fence.

Cottage in Sandhurst

4.97 out of 5 average rating, 370 reviews

The Cabin - a little ranch house. A peaceful haven

Located in the High Weald area of Kent which is an AONB, The Cabin at Valley View Farm is set in its own space amongst 16 acres of wood and grazing. It used to be an old hop pickers mobile home but has been lovingly restored to a modern, well presented “mini” haven. A fully self-contained cabin with open plan lounge/dining/kitchen area, UK king size bed in bedroom and a shower room and toilet. Ideal for a couple or two singles as a Z-bed can be provided. Private outside veranda with a fire pit

Top guest favorite

A charming cottage is surrounded by a gravel courtyard, featuring white wood paneling and a traditional tiled roof. Greenery adorns the walls and a small garden area is visible at the entrance. The landscape includes trees in the background, contributing to a serene rural setting.

Cottage in Sandhurst

5 out of 5 average rating, 408 reviews

Cosy Cottage with Woodburner & Countryside Views.

Cowbeach Cottage is Grade II listed and has been lovingly restored to a high standard. It features a wealth of old oak beams and an inglenook fireplace with a cosy wood burning stove. It is tastefully decorated throughout to provide a relaxing space. The bespoke oak staircase leads to a beautiful vaulted bedroom with views across the Kent countryside. The cottage benefits from a private south facing garden and patio. It is ideally situated to explore the many National Trust properties close by.

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 in East Sussex

4.97 out of 5 average rating, 307 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.

Guest favorite

An inviting outdoor patio features a rustic wood-fired oven, surrounded by greenery. Comfortable lounge furniture and a wooden table are present, with potted plants adding a touch of nature. A patterned area rug enhances the space, creating an ideal spot for relaxation.

Cottage in Kent

4.9 out of 5 average rating, 142 reviews

Idyllic 2- Bedroom barn with amazing views

Spacious barn conversion with views of the countryside. The Barn is an ideal location to use as a base for visiting the many places of interest or for a relaxing holiday. There are many National Trust properties within a small radius together with historic gardens and local vineyards. Tenterden and Rye are a short drive and Camber Sands, with its sandy beach, is a must. There are a number of local pubs which serve food, The White Hart within a few minutes walk, and many others not far away.

Top guest favorite

An inviting interior showcases a dining area with a dark table and patterned chairs. The living space features comfortable seating, a TV console, and warm lighting. Large windows allow natural light to illuminate the space, while a subtle division between areas can be observed.

Cottage in Rye

4.97 out of 5 average rating, 178 reviews

Willow Cottage, Hot tub & Coastline views, Rye

My place is close to Rye & the beaches of Camber Sands & Winchelsea. October-March late checkout on Sundays (4pm), midweek stays enjoy a discounted rate. The perfect spot to unwind, beautiful countryside & sea air, amazing views from the private garden & terrace to the English Channel. Willow Cottage is the wing to the main house once owned by the comedian & author Spike Milligan. Newly renovated & fully refurbished to a high modern standard, with a brand new kitchen & two new bathrooms.

Guest favorite

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 in Peasmarsh

4.89 out of 5 average rating, 177 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.

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 in Winchelsea Beach

4.95 out of 5 average rating, 110 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

The indoor swimming pool features clear, inviting water surrounded by lush greenery. Large windows allow natural light to fill the space, offering views of the private garden. Comfortable seating is positioned along the edges, creating a relaxing atmosphere for guests.

Cottage in East Sussex

4.97 out of 5 average rating, 278 reviews

Badgers Den - Covehurst Bay Holiday Cottage

Luxury self-catering holiday cottage in the countryside near Hastings. Heated indoor swimming pool, steam room, gym & outdoor hot tub. 2 bedrooms and 2 bathrooms, suitable for up to 4 people. Kitchen, dining & living room is open plan with large Smart TV & free Netflix. 2 bathrooms. Free high speed WiFi throughout. Sunny conservatory, private garden with sun loungers & BBQ. Amazing coastal and countryside walks right from the doorstep.

Superhost

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 in East Sussex

4.82 out of 5 average rating, 309 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.

Guest favorite

A private garden is shown, featuring a grassy area with stepping stones leading towards a turquoise door. Surrounding greenery includes shrubs and flowering plants, contributing to a natural and tranquil setting.

Cottage in Hastings

4.92 out of 5 average rating, 317 reviews

Charming Little Worker’s Cottage

Built in the 1860’s this little rustic one bedroom workers cottage is a place to relax and a base for exploring. Situated in 0re, nearby paths lead to the beautiful Hastings Country Park Nature Reserve with its coastal country walks, ancient woodlands and dramatic clifftop sea-views. Set back from the road, along a terrace of small cottages, this is a place for quiet and bird song.