Holiday houses in Winchelsea

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Top-rated holiday rentals in Winchelsea

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Top Guest favourite
A quaint outdoor seating area features two white metal chairs and a central round table. A wooden bench with heart-shaped cutouts serves as additional seating, adorned with soft cushions. A tray on the table holds a cup and a pastry, surrounded by lush greenery.
Home in England
5 out of 5 average rating, 218 reviews

The Place in Rye - Peaceful, spacious cottage

The Place in Rye is located in The Mint in the very centre of historic Rye, and sleeps 4. The newly renovated cottage has two light and airy bedrooms each with king size beds, ample storage space and their own luxury bathroom. There is a new fitted kitchen, dining area and comfortable sitting room, WIFI, smart TV and small library. There is a peaceful sunny courtyard with outside seating for 4. There is a car park 50 meters from the cottage. Sorry we do not accept children under 12 and no pets.

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 Pett
4.98 out of 5 average rating, 336 reviews

Pebbles - calm 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 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 Beckley
4.89 out of 5 average rating, 188 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 spacious living area features large windows that frame captivating sea views. A wooden dining table is set between the windows, accompanied by two chairs. A plant is placed on each side of the room, and simple furnishings are styled for a relaxed atmosphere.
Apartment in Hastings
4.99 out of 5 average rating, 144 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
4.95 out of 5 average rating, 114 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.

Guest favourite
The charming exterior of the seaside cottage is showcased, featuring a light green front door framed by blooming pink flowers and lush greenery. A wooden bench is positioned on a path leading to the entrance, set against a clear blue sky.
Home in Rye Harbour
4.94 out of 5 average rating, 368 reviews

Charming, Cosy Cottage in Rye Harbour

Light and airy seaside cottage with lots of character. Built in around 1900, it was originally home to one of the local coastguards who were stationed in the village. Cosy and comfortable sitting room. Open plan kitchen diner opening in to the sunny sheltered garden. The kitchen is well equipped, with microwave, electric oven, washer dryer and dishwasher. There is a double bedroom and a single room with bunk beds. The family bathroom is downstairs,and we have an upstairs toilet.

Top Guest favourite
A cobbled street lined with traditional timber-framed houses showcases the architectural charm of the area. The buildings feature decorative leaded glass windows and steep roofs, with greenery and street lamps adding to the historic ambiance. A clear sky can be seen above.
Home in East Sussex
4.98 out of 5 average rating, 214 reviews

14th-Century House in Rye's Historic Citadel

Hucksteps is a medieval, 3 bedroom/2 bathroom house centrally located in the Citadel of Rye. Facing St Mary’s Church, the house is surrounded by cobbled streets, period architecture, literary associations, stunning coastline, and vibrant culture. Camber's sandy beaches and dunes are an easy walk/cycle/drive away. A High Street full of independent shops, restaurants, inns, art galleries, Kino cinema, Rye Spa Retreat, tea rooms are round the cobbly corner.

Top Guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 844 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Top Guest favourite
A charming view of Mermaid Street is captured, showcasing an array of historic buildings with black and white exteriors. Cobblestone paths wind through the scene, accompanied by neatly trimmed hedges and planters. A decorative sign hangs above, adding character to the quaint street.
Condo in East Sussex
4.95 out of 5 average rating, 342 reviews

Grade II listed apartment in Mermaid Street, Rye

A grade II listed apartment in the centre of Rye. The property is situated at the bottom of famous cobbled Mermaid Street through a courtyard entrance on The Mint. It is a short walk to local pubs, restaurants and fish and chip shops with beaches within a 10 minute drive. The property features a quirky steep winded staircase and is set on 3 floors! These are also super steep so please be careful with children. A 10 minute walk from Rye station.

Guest favourite
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 Udimore
4.83 out of 5 average rating, 334 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
A charming bedroom is highlighted by a striped headboard adorned with decorative pillows. An accented wall in warm tones complements framed artwork above the bed. A small tray table holds a vase with fresh flowers, adding a touch of color and elegance to the space.
Home in East Sussex
4.98 out of 5 average rating, 130 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.

Top Guest favourite
A well-equipped kitchen features open shelving displaying dishes and cookware. Light wood flooring extends into a cozy living area with large glass doors opening to a garden. A dining table is positioned nearby, enhancing the space's functionality and warmth.
Bungalow in Winchelsea Beach
4.9 out of 5 average rating, 452 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