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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

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.

4.94 out of 5 average rating, 202 reviews
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 in Icklesham

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.

4.97 out of 5 average rating, 278 reviews
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

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.

4.98 out of 5 average rating, 136 reviews
Superhost
Cottage in Fairlight

Sunny single-level cottage • Dogs • Near Rye

Escape to our bright, single-level Sussex cottage, perfect for relaxed coastal breaks with family, friends, or older relatives. Minutes from the sea, historic Rye and trendy Hastings, the cottage offers a sunny interior, enclosed garden, parking and a peaceful setting ideal for unwinding after coastal walks or countryside days out. Dog-friendly and thoughtfully laid out with no stairs, it’s an easy and comfortable base for exploring the best of East Sussex, from beaches to charming villages.

4.84 out of 5 average rating, 271 reviews
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 Rye

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.

4.95 out of 5 average rating, 151 reviews
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

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.

4.98 out of 5 average rating, 171 reviews
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

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.

4.97 out of 5 average rating, 377 reviews
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

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.

4.94 out of 5 average rating, 130 reviews
Top Guest favourite
The cozy living room features a traditional brick fireplace as its focal point. A comfortable sofa is complemented by an armchair and a wooden coffee table. Shelving displays various decorative items, while a television is positioned to the left. Soft lighting is provided by a stylish chandelier.
Cottage in Rye

Daisy Tatham Cottage, Rye

Daisy Tatham Cottage is perfectly situated in the heart of the historic Cinque Ports town of medieval Rye, East Sussex – in 1066 country. ‘Daisy’ is a Victorian terraced house dating from about 1850 and provides comfortable, charming and dog friendly accommodation for up to five people. The 5th bed is a futon style single sofa. The house is walking distance from the railway station and just minutes away from Rye's most loved pubs and restaurants.

4.99 out of 5 average rating, 207 reviews
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

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.

4.82 out of 5 average rating, 369 reviews
Top Guest favourite
The exterior of the cottage showcases a landscaped garden with a stone patio and wooden seating. Flower beds add color beside the entrance, while a gravel driveway leads to an attached garage. Lush greenery surrounds the property, creating a serene outdoor setting.
Cottage in Hastings

Swallows Nest Cottage with Pool & Spa

Luxury self-catering holiday cottage in the countryside by Covehurst Bay, Hastings. Heated indoor swimming pool, steam room, gym & outdoor hot tub. Two bedrooms, both en-suite, suitable for up to 4 people. Free high speed wifi throughout. Kitchen, dining & living room is open plan. Private garden with glass veranda over patio, pool table & BBQ. Large smart TV's with free Netflix. 20 minute walk to the beach.

4.97 out of 5 average rating, 216 reviews
Top Guest favourite
The charming exterior of a white cottage is framed by blooming lavender plants in the foreground. The entrance features a small, peaked roof and a door with a window, adding character to the inviting facade. Green grass surrounds the cottage, enhancing its appeal.
Cottage in East Sussex

Period Cottage, Iden, Rye, East Sussex. Sleeps 6

Lavender Cottage is located in the picturesque village of Iden, East Sussex. Renowned as an Area of Oustanding Natural Beauty, the village was first mentioned in the Domesday book. Dating back to the 17th Century, the pretty cottage with its wonky floors, low ceilings, inglenook fireplace and abundance of character, is the perfect base for exploring this medieval part of the country.

4.97 out of 5 average rating, 104 reviews

Popular amenities for Winchelsea cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
A charming thatched cottage is surrounded by meticulously maintained gardens featuring geometric hedges and a stone pathway. Lush greenery and trees frame the scene, while a tranquil pond reflects the clear sky above.
Cottage in Rotherfield

The Granary, Organic Vineyard stay with Pool.

4.98 out of 5 average rating, 371 reviews
Guest favourite
A charming thatched cottage is surrounded by a well-kept garden, featuring colorful flower beds and neatly trimmed hedges. The cottage's white walls contrast with the natural thatch roof, while scenic green fields extend in the background, adding a peaceful countryside ambiance.
Cottage in Appledore

Cosy Thatched Cottage in Kent | Hot Tub | Sleeps 6

4.93 out of 5 average rating, 126 reviews
Top Guest favourite
The cottage is set in lush, mature grounds, surrounded by trees and colorful shrubs. A gentle stream meanders through the garden, with seating areas visible among the greenery. The house features a sunlit facade, offering a serene view of the countryside.
Cottage in Kent

Daweswood Cottage Guest Favourite, hot tub & lake

4.96 out of 5 average rating, 323 reviews
Top Guest favourite
The barn is framed by greenery, with a spacious lawn in the foreground. The exterior features a dark wooden façade and a moss-covered roof. Sunlight illuminates the tranquil surroundings, inviting relaxation in this rural setting.
Cottage in Smeeth

Evegate Manor Barn

4.97 out of 5 average rating, 813 reviews
Guest favourite
A charming cottage exterior is framed by lush greenery and mature trees. The building features a traditional wooden door and a large window, allowing natural light to fill the interior. Gravel pathways lead to the entrance, enhancing the rustic appeal of the setting.
Cottage in Detling

Cottage in the Wood, Detling

4.85 out of 5 average rating, 213 reviews
Guest favourite
A spacious garden area features neatly trimmed grass, alongside blooming trees and hedges. A circular patio table with several chairs provides an inviting spot for outdoor dining. A large conservatory is visible, allowing for a seamless connection between indoor and outdoor spaces.
Cottage in Challock

Idyllic Cottage with Private Hot Tub

4.87 out of 5 average rating, 157 reviews
Top Guest favourite
Cottage in Littlebourne

'Bramble Lodge' Littlebourne, Canterbury (hot tub)

4.93 out of 5 average rating, 494 reviews
Top Guest favourite
Cottage in Kent

Oak Cottage: Hot Tub, Large Patio & Alpaca Views

4.95 out of 5 average rating, 169 reviews

Pet-friendly cottage rentals

Guest favourite
A charming stable conversion is set within a green landscape, featuring a low fence and neatly trimmed hedges. The front patio area offers a seating arrangement beside well-maintained grass, with the rustic brick exterior showcasing traditional architectural elements and a thatched roof beneath a partly cloudy sky.
Cottage in Brookland

Peaceful Idyllic Stable on Romney Marsh near Rye

4.89 out of 5 average rating, 507 reviews
Superhost
Cottage in Camber Sands

Saltwater Cottage - Camber Sands near Rye

4.9 out of 5 average rating, 332 reviews
Top Guest favourite
The charming exterior of the cottage features a combination of red brick and stone, with a pitched gray roof. A covered entrance is flanked by small potted plants, and a spacious outdoor area includes a picnic table, surrounded by wooden fencing and lush greenery.
Cottage in Wadhurst

Castle Cottage, Wadhurst

4.95 out of 5 average rating, 100 reviews
Top Guest favourite
Cottage in Ticehurst

Ticehurst Home with a view

4.95 out of 5 average rating, 341 reviews
Guest favourite
A view of the coast features a rocky shoreline with large stones protecting the waterfront. Beyond the rocks, a collection of cottages is visible under a colorful sky at sunset, blending shades of orange, pink, and purple.
Cottage in Jurys Gap, East Sussex

Coastguards Lookout

4.88 out of 5 average rating, 148 reviews
Top Guest favourite
The traditional square kiln oast stands prominently, showcasing its distinctive tiled roof and white wooden features. Lush greenery and blooming flowers surround the property, with a clear blue sky enhancing the tranquil setting. A well-maintained garden path leads towards the entrance.
Cottage in Kent

Delightful pet-friendly oast with private garden

4.99 out of 5 average rating, 130 reviews
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

Peace, Quiet, Cosy house with garden & log burner

4.9 out of 5 average rating, 206 reviews
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

Charming Little Worker’s Cottage

4.92 out of 5 average rating, 390 reviews

Private cottage rentals

Top Guest favourite
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

Cosy Cottage with Woodburner & Countryside Views.

5.0 out of 5 average rating, 457 reviews
Guest favourite
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

Idyllic 2- Bedroom barn with amazing views

4.91 out of 5 average rating, 171 reviews
Guest favourite
A comfortable living area is presented with two leather sofas and a large coffee table. A flat-screen TV is positioned on a glass stand. Natural light enters through the window, illuminating the room's neutral tones and indoor plants.
Cottage in East Sussex

Tranquil Hastings Hideaway: Escape to Our Cottage

4.95 out of 5 average rating, 164 reviews
Superhost
A cozy window nook features cushioned seating highlighted by two decorative pillows. A small white table is set with a decorative plant and a candle, while natural light filters through the white blinds, creating a bright yet serene atmosphere.
Cottage in Rye

Cosy 2 Bedroom Cottage In Rye

4.83 out of 5 average rating, 214 reviews
Top Guest favourite
An open-plan living area is presented, featuring a wooden dining table set with white dishes and cutlery. In the background, a comfortable couch is adorned with plaid cushions, and a large mirror reflects the cozy ambiance. A soft rug enhances the space.
Cottage in Rye

Ockman Cottage in the citadel Rye

4.93 out of 5 average rating, 193 reviews
Top Guest favourite
A sandy beach stretches toward the horizon, with gentle ripples in the water reflecting sunlight. Delicate tufts of grass are seen in the foreground, adding texture to the landscape against a clear blue sky dotted with a few fluffy clouds.
Cottage in Camber Sands

Stunning Camber Sands holiday retreat

4.98 out of 5 average rating, 141 reviews
Top Guest favourite
The open-plan living area features exposed wooden beams, enhancing the spacious feel. Comfortable sofas are arranged around a wooden coffee table, with a TV visible in the corner. A fully equipped kitchen is positioned in the background, integrating modern functionality with rustic charm.
Cottage in Tenterden

Pickle Cottage Tenterden

4.97 out of 5 average rating, 580 reviews
Guest favourite
A sunset is captured over the water, displaying vibrant hues of orange and yellow against a serene sky. The reflective surface of the water mirrors the colors, creating a tranquil atmosphere. The sandy beach stretches along the foreground, enhancing the peaceful scene.
Cottage in Rye

Mayfayre - 2 Bed Cottage Beside the Beach

4.96 out of 5 average rating, 427 reviews

Destinations to explore