Holiday houses in Winchelsea

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Top-rated holiday rentals in Winchelsea

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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.

Guest favourite
Barn in Brede Rye
4.95 out of 5 average rating, 180 reviews

The Lodge at Maidlands Oast - Nr Rye, East Sussex

Maidlands Lodge is a detached converted barn boasting stunning uninterrupted far reaching views across the Tillingham Valley. It provides guests the ultimate luxury retreat and romantic getaway for two nestled in the heart of the breathtaking rolling East Sussex countryside . This light and airy property is presented to the highest of standards throughout providing top quality linens and bedding as standard. The underfloor heating also ensures a cosy retreat throughout the winter months.

Top Guest favourite
An open-plan living space features a dark sofa with colorful cushions, enhancing the relaxed ambiance. A generous dining table is set for meals, accompanied by wooden chairs. Windows allow natural light to flood the room, providing a view of the surrounding landscape.
Home in Kent
4.99 out of 5 average rating, 116 reviews

Beach house in Dungeness

Beautiful Dungeness house right on the beach with ever changing views of the sea all year round. The house incorporates an original train carriage and the living space is open plan. The well equipped kitchen includes a generous dining table and chairs, which also looks out across the beach. There are two double bedrooms within the carriage as well as a shower room. An ideal place to explore Dungeness as well as discovering the wider area including Rye, Folkestone and the Romney Marsh.

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, 357 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.

Guest favourite
Apartment in Hastings
4.99 out of 5 average rating, 160 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 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
4.94 out of 5 average rating, 119 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
A self-built studio cabin is presented in a peaceful outdoor setting, featuring a red roof and dark wooden exterior. A small patio area with two chairs is visible at the front. Nearby, a wooden storage unit adds functionality to the space.
Cabin in Rye Harbour
4.96 out of 5 average rating, 154 reviews

The Other Red Hut

Unique self built studio cabin in a peaceful setting only a stones throw away from the Nature Reserve - replicating the well known Red Hut in Rye Harbour. PLEASE NOTE : The wc/shower room is A SEPARATE building adjacent to the main hut. The sink area is also outside the hut. There’s a patio area which looks towards the Martello tower (The enchantress) There is also a seating area at the bottom of the garden. A sun umbrella when sitting outside is available for your use also.

Top Guest favourite
A panoramic view showcases the coastline of Rye Bay under a clear blue sky. The image captures the serene sea and sandy beach lined with sparse vegetation, while the distant shoreline is visible. The landscaped area and nearby structures provide context to the scenic setting.
Home in East Sussex
4.97 out of 5 average rating, 102 reviews

Beachfront views of Rye Bay, with EV charger.

Beach-front views of Rye Bay, a spacious modern house set above the beach on a private lane. Its four bedrooms enjoy sea views and there's room on the balcony to relax in the morning sun. The second floor Belvedere (lookout) gives extensive views across Rye bay to English Channel. A great base for exploring Hastings, Rye and East Sussex, or simply going to the beach. There are 32 steps up to the house. 7kW EV charger, bring your type 2 cable (pay online per kWh). Pet free.

Guest favourite
The exterior of Hop Pickers Retreat is showcased, featuring a wooden facade with large glass windows. A spacious deck area includes seating and a woodfired hot tub, surrounded by greenery. The structure blends modern and natural elements, providing a serene outdoor space.
Cabin in East Sussex
4.95 out of 5 average rating, 205 reviews

Relaxing Luxury Retreat

Hop Pickers Retreat is found in the heart of an Area of Outstanding Natural Beauty (AONB) on the Kent and East Sussex border. Located on an farm you are surrounded by wildlife, birdsong, mooing cows, stunning views and in the summertime the sound of a combine, combining the crops in the surrounding fields. It is the ideal place to turn off that phone and unwind with your glass of your favourite tipple in the woodfired hot tub underneath the big starry sky.

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
4.83 out of 5 average rating, 351 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 favourite
Home in Rye
4.99 out of 5 average rating, 162 reviews

The Yard Rye

The Yard is a two-bed interior-designed cottage in the citadel of the beautiful Cinque Port town of Rye. It is situated down a cobbled passageway next to a pretty tea room. PLEASE NOTE – The property can sleep up to two adults in the master bedroom and one child in the single, with a pull-out camp bed if needed for an extra child. We also have a travel cot for an infant. Please be aware we have a steep staircase.

Superhost
Bungalow in Winchelsea Beach
4.9 out of 5 average rating, 470 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.

Popular amenities for Winchelsea holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. East Sussex
  5. Winchelsea