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, 216 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 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
5 out of 5 average rating, 426 reviews

Cosy Cottage with Woodburner & Countryside Views.

Cowbeach Cottage is Grade II listed and has been lovingly restored to a high standard. It features a wealth of old oak beams and an inglenook fireplace with a cosy wood burning stove. It is tastefully decorated throughout to provide a relaxing space. The bespoke oak staircase leads to a beautiful vaulted bedroom with views across the Kent countryside. The cottage benefits from a private south facing garden and patio. It is ideally situated to explore the many National Trust properties close by.

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, 333 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 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, 141 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 retreat's exterior is characterized by modern architecture, featuring large arched windows and a welcoming entrance. Surrounding greenery, including tall trees, enhances the natural setting, while a gravel pathway leads to a spacious outdoor area with wooden seating and potted plants.
Cabin in East Sussex
4.95 out of 5 average rating, 181 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.

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, 332 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, 128 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, 450 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.

Guest favourite
A charming two-story beach house is presented with a dark exterior and white trim. A stone pathway leads to the front door, flanked by well-maintained greenery. Large windows invite natural light into the interior, while a detached structure is visible to the side.
Home in Winchelsea Beach
4.87 out of 5 average rating, 225 reviews

Beautiful Beach House Winchelsea Beach East Sussex

Beautiful 3-bedroom beach house (double, twin, bunk). 100m to Winchelsea Beach. Sea views from lounge and master bedroom balconies. Garden with deck area and outdoor table and chairs. Walking, cycling, water-sports, bird-watching (Rye Harbour Nature Reserve). The Ship deli (great butchers and bread!) and the Red Pig food truck. Good pubs, restaurants and cafes in Rye and Icklesham.

Top Guest favourite
A detached cottage is showcased with a well-maintained garden and a wooden deck. A rose bush climbs the trellis at the forefront, while an open grassy space extends to the back, framed by rustic fencing and trees in the background.
Guest suite in Icklesham
5 out of 5 average rating, 213 reviews

Valley View Cottage

We would like to welcome you to our detached cottage in the small village of Icklesham, between Hastings and Rye. With open countryside on the doorstep, there are plentiful walks including the 1066 Country Walk which runs long side the property. With comfortable space both inside and out, you can also just take it easy and enjoy the peace and tranquillity on offer.

Guest favourite
A modern kitchen is presented with light blue cabinetry and a wooden countertop. Open shelves display dishware and glassware, while a playful pig silhouette adorns the wall. Stainless steel appliances and a gas stove integrate functionality, creating a welcoming cooking space.
Farm stay in Rye Foreign
4.97 out of 5 average rating, 174 reviews

The Bullock Lodge, Lea Farm, Rye Foreign

The Bullock Lodge is situated on a fifth generation working farm in the Sussex countryside known as Rye Foreign. Nestled in its own quiet valley with beautiful views out stretching to neighbouring Rye and across to Tillingham, it’s the perfect bolt hole for peace and quiet amongst nature but with beaches and the historic town of Rye only a stones throw away.

Popular amenities for Winchelsea holiday rentals

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