Cottage vacation rentals in Winchelsea

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Top-rated cottage rentals in Winchelsea

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Guest favorite

A serene beach scene at sunset, featuring a gradient of orange and pink hues in the sky. The water reflects these colors, and the shoreline is outlined by a rocky cliff in the distance. Patches of exposed sand and scattered wooden posts are visible along the beach.

Cottage in Pett Level

4.94 out of 5 average rating, 151 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 vintage wooden high chair is positioned next to a traditional sink, showcasing its simple and sturdy design. Dark wooden cabinet with rounded knobs sits nearby against a backdrop of intricately patterned tiled flooring.

Cottage in Brook

4.99 out of 5 average rating, 185 reviews

Charming historic cottage in the North Kent Downs

Situated in the Kent Downs Area of Outstanding Natural Beauty, this 18th century cottage offers a relaxing and comfortable stay with its own private garden. The Kent coast is easily accessible by car (Deal, Folkestone, Hythe & Dungeness) as is the historic town of Canterbury. The house is perfectly located for a short break from London (15-minute taxi from Ashford International) or a stopover when travelling to or from the Continent with the Eurotunnel and Dover Port within 30 minutes drive.

Top guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 287 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

Cottage in Kent

4.91 out of 5 average rating, 132 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.

Guest favorite

A hot tub is featured in a private outdoor space, with water gently bubbling. Sunlight reflects off the water surface, while surrounding greenery creates a sense of privacy. A nearby door suggests easy access to the interior of the cottage.

Cottage in Rye

4.96 out of 5 average rating, 169 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 small wooden table is set outdoors, accompanied by two glasses, a bottle, and a vase with flowers. A nearby green apple rests on the table, while greenery and a tranquil water feature create a peaceful backdrop.

Cottage in Peasmarsh

4.91 out of 5 average rating, 165 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.

Superhost

An aerial view captures the three Coastguard Cottages nestled near a wide expanse of beach. The cottages showcase a blend of traditional architecture with updated features. The shimmering sea reflects sunlight, while a stretch of grassy land separates the cottages from the shoreline.

Cottage in Camber

4.85 out of 5 average rating, 115 reviews

Coastguards Lookout

★ "The house was all we could have hoped for. The location just a stone’s throw from the sea was stunning..." Wake in comfort to the sound of the sea, explore the misty brooding Romney Marsh, then warm up in the many atmospheric pubs with intriguing histories, resident ghouls, roaring fireplaces, cracking ales and tasty pub grub, walk along our pebbled beach, look out across the shimmering blue sea and you’ll feel like you’ve discovered another world.

Top guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 272 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.

Guest favorite

A well-kept pathway leads alongside a charming cottage, bordered by lush greenery and colorful blooming flowers. A person is seen tending to the garden, while others stroll along the path, enjoying the peaceful surroundings. A classic streetlamp provides soft illumination, enhancing the tranquil ambiance.

Cottage in Playden

4.88 out of 5 average rating, 226 reviews

Characterful cottage for two on quiet farm lane

Willow cottage is a one bedroom detached home on a quiet farm lane in Playden, 2 mins drive from Rye, the historic cinque port town. The perfect cottage for a couple (plus baby) to relax in. There are plenty of country walks direct from the cottage and Camber Sands and Winchelsea beaches a 10mins drive away. There is a dedicated parking space outside. The owners are next door to give you local recommendations if required.

Top guest favorite

Cottage in Rotherfield

4.98 out of 5 average rating, 302 reviews

The Granary at Coes Vineyard, East Sussex

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.

Superhost

The exterior of a stone cottage is featured, showcasing a sloped roof with gray shingles. A red door offers entry, framed by two large windows. The surrounding landscape includes greenery, with a gravel path leading to the entrance and wooden fencing nearby.

Cottage in East Sussex

4.81 out of 5 average rating, 289 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 coastal scene displaying a view of the sea alongside a rugged cliff. Lush green vegetation lines the path in the foreground, leading towards the bluffs. The sky is partly cloudy, creating a serene atmosphere over the tranquil waters.

Cottage in Hastings

4.92 out of 5 average rating, 297 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.