Cottage holiday rentals in Winchelsea

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Top-rated cottage rentals in Winchelsea

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Guest favourite
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
4.94 out of 5 average rating, 190 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 favourite
The private garden features a well-maintained grassy area surrounded by trees. The cottage is visible with large glass doors leading to a terrace. Two lounge chairs are positioned on the patio, offering a spot to enjoy the outdoor scenery.
Cottage in East Sussex
4.99 out of 5 average rating, 119 reviews

Birch Cottage, Rye, Coastline Views & Hot Tub

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. It is a perfect spot to unwind combining beautiful countryside with sea air and amazing views from the private garden and terrace of the English Channel. Birch Cottage in the grounds of the main house once owned by the comedian & author Spike Milligan. Newly renovated to a high modern standard, with a brand new kitchen & two new bathrooms.

Top guest favourite
A charming cottage displays a wooden shingle exterior with a distinctive green door. The two-story structure features multiple windows, inviting natural light. The well-maintained facade is complemented by a cobblestone pathway, reflecting the historic character of its surroundings.
Cottage in East Sussex
4.95 out of 5 average rating, 132 reviews

23 Tower St., Landgate Cottage, Rye

Landgate Cottage is ideally located, opposite the remaining 14th Century Landgate entrance to the old citadel in the heart of Rye. Everything is nearby, with shops, tea rooms, bistros, pubs, restaurants and the Kino Rye cinema also. There is fantastic access to coast and countryside. Close to car parks (£3.00 / 24 hrs), bus stops and Rye railway station (London St Pancras is an hour and 4 mins). Two double bedrooms, bath, shower, fully equipped kitchen and outside terrace with seating.

Top guest favourite
An outdoor dining area features a long, rustic table paired with sturdy benches. Subtle outdoor lighting illuminates the setting, creating a serene atmosphere. Decorative cushions rest on the benches, and a cozy blanket is draped over one, enhancing the inviting space for gatherings.
Cottage in East Sussex
4.98 out of 5 average rating, 159 reviews

Driftwood is a 2 minute stroll to Pett Level Beach

A perfect blend of stunning coast and countryside on the doorstep. Driftwood is a beautifully renovated three bedroom beach house that’s two minutes stroll from the beach and surrounded by miles of beautiful countryside including spectacular cliff top walks. Historic Rye and Camber Sands are a short drive away. The house is unassuming from the outside, and once you’re inside it feels light, warm and welcoming with a Scandi vibe. All rooms are on one spacious floor. Dogs are very welcome.

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 in Peasmarsh
4.9 out of 5 average rating, 196 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 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, 353 reviews

Pebbles - a calm and peaceful retreat near the sea

Pebbles is a place to relax and unwind, situated in a private annexe at our home in Pett Level. You’ll be only five minutes walk from an amazing beach. Surrounded by beautiful 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. Pebbles has a lounge overlooking the garden, double bedroom, wet room and a fully fitted kitchen. The garden is secluded and peaceful . The beautiful town of Rye is 5 miles 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 in Winchelsea Beach
4.95 out of 5 average rating, 118 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 favourite
The exterior of the eco-friendly cottage is framed by an array of flowering plants and gravel pathways. Natural wood cladding complements the blue sky. Outdoor seating includes a dining table and chairs, inviting relaxation in the spacious garden area.
Cottage in Brightling
5 out of 5 average rating, 166 reviews

The Long Stable: Rural haven, spacious, fast Wifi

Stylishly fitted and eco-friendly, our detached, self-contained cottage is in a very rural location. There are no other holiday cottages on the farm. Situated in the High Weald Area of Outstanding Natural Beauty, on a sheep farm of 23 acres (which you are free to roam), this is a real get-away-from-it-all location. One of the most peaceful and relaxing places you will ever stay. With underfloor heating and a wood-burning stove you will be cosy whatever the weather.

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, 348 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 favourite
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, 372 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.

Top guest favourite
Cottage in Ticehurst
4.95 out of 5 average rating, 331 reviews

Ticehurst Home with a view

Cottage This two bedroomed cottage is set down a quiet lane adjacent to Bewl Water, which is the largest stretch of open water in the South East. The 800 acre site is set in an Area of Outstanding Natural Beauty, in the heart of the High Weald and very popular with walkers, cyclists and fishermen.

Top guest favourite
A spacious living area showcases exposed wooden beams and tall ceilings. Natural light filters through the windows, illuminating a mix of seating options, including a green sofa, armchairs, and various tables. Artwork adorns the walls, contributing to a cozy atmosphere.
Cottage in Golford
4.98 out of 5 average rating, 255 reviews

Charming cottage with minstrels gallery in 7 acres

A cosy, light and spacious traditional oak-framed building with a minstrels' gallery and a full height living area. Standing in seven acres of private grounds, on the path of an ancient but now forgotten travellers' way, Whistlers is surrounded by meadows, orchards and woodland walks.

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