Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

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Top guest favorite
A comfortable lounge area features a mix of seating, including a light-colored sofa and an orange accent chair. The space is complemented by a wooden coffee table, a large area rug, and natural light from the window. A wall-mounted TV and decorative shelves add character.
Home in Winchelsea
4.98 out of 5 average rating, 101 reviews

Stylish, quiet bungalow in Winchelsea Beach

A renovated bungalow nestled in a quiet cul-de-sac in a peaceful seaside village. On the verge of a bustling nature reserve and a short walk or bike ride to the beautiful coastline, this home has everything you need to explore the local area. The shingle beach is glorious any time of year and quieter than other local beaches. There are easy walks to Pett Level, Rye or to inland villages (and wonderful local pubs). Being close to Pett Pools and Rye Harbour, it is ideal for birdwatchers.

Top guest favorite
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
4.98 out of 5 average rating, 372 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 favorite
An inviting interior showcases a dining area with a dark table and patterned chairs. The living space features comfortable seating, a TV console, and warm lighting. Large windows allow natural light to illuminate the space, while a subtle division between areas can be observed.
Cottage in Rye
4.97 out of 5 average rating, 226 reviews

Willow Cottage, Hot tub & Coastline views, Rye

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. The perfect spot to unwind, beautiful countryside & sea air, amazing views from the private garden over English Channel. Tennis court in main gardens available for guest use. Willow Cottage is the wing to the main house once owned by the comedian & author Spike Milligan. Newly renovated & fully refurbished to a high modern standard.

Guest favorite
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, 174 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 favorite
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, 127 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 favorite
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, 213 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.

Top guest favorite
Home in Rye Harbour
4.97 out of 5 average rating, 105 reviews

Cosy cottage in Rye Harbour

Welcome to our idyllic sea-side cottage in Rye Harbour, just down the road from a cosy pub, a village store, and a nature reserve. The nature reserve is ideal for walks and birdwatching, and is home to the Discovery Centre where you can grab a coffee and learn about the area. There are lots of pubs, cafes, restaurants & a winery in Rye town, 5 minutes away by car. The house is also conveniently located for day trips to Winchelsea and Camber Sands.

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, 364 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 favorite
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 Rye
4.99 out of 5 average rating, 180 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.

Guest favorite
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, 480 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.

Top guest favorite
A cozy sitting area features a dark sofa adorned with colorful cushions, set against a rustic stone wall. The space includes a woven basket and a light fixture made of natural materials. Windows allow for natural light to illuminate the room's warm tones.
Apartment in Rye
4.97 out of 5 average rating, 355 reviews

The Stables, Rye

A characterful and charming property in the Ancient Town and Cinque Port of Rye. Recently renovated 'The Stables' is believed to have originally formed a part of Rye's original town wall and benefits from a wealth of period charm. Located at the bottom of Mermaid street and opposite the bustling Strand, you will find antique shops scattered amongst restaurants a stones throw away!

Superhost
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
4.86 out of 5 average rating, 230 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.

Popular amenities for Winchelsea vacation rentals