Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

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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

4.97 out of 5 average rating, 307 reviews

Pebbles - calming 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.

Top 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, 106 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

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

4.95 out of 5 average rating, 110 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 favorite

Barn in East Sussex

4.94 out of 5 average rating, 208 reviews

Tillingham View near Rye

A converted steam engine house, Tilingham View has far reaching views of open countryside, the Tillingham Valley and beyond to Rye. Benefitting from a woodburning stove and mezzanine bedroom with a window overlooking the wonderful view. A very pretty garden is shared with the owner. One well behaved dog welcome. There is a fully equipped kitchen with microwave, electric oven and hob. In the lounge is a Smart TV with full TV package and BT Sport.

Top guest favorite

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, 185 reviews

Unique 14th century house in the Citadel of Rye

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 is round the cobbly corner.

Top guest favorite

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, 315 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.

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, 309 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.

Guest favorite

A spacious sleeping area features a comfortable bed dressed in light linens and a bright yellow blanket. The decor includes soft pillows and artwork decorates the walls. A kitchenette is visible in the background, along with a small dining area bathed in natural light from the skylight above.

Apartment in Fairlight

4.94 out of 5 average rating, 182 reviews

Cosy Fairlight Studio Flat

Our cosy studio apartment is in a quiet private Cul-De-Sac. We are within walking distance of the beautiful cliff top walks of the Hastings Country Park and Firehills with its spectacular views across the Sussex coast. Hastings old town, the medieval town of Rye and historic Battle are a short drive away. The property is surrounded by trees and hedgerows and there is a secluded front garden to eat outside in the summer.

Guest favorite

An open plan living area is presented with a cozy seating arrangement, featuring a comfortable armchair and a vintage trunk coffee table. A dining area with a round table and white chairs is visible, along with a decorative fireplace and a cheerful bouquet of flowers.

Apartment in East Sussex

4.94 out of 5 average rating, 248 reviews

Hamiltons Nest

Romantic holiday apartment centrally located in the medieval town of Rye Stylishly decorated throughout to offer comfortable accommodation Within walking distance of Rye’s independent shops, cafes and restaurants Close to Camber Sands beach, Rye Harbour Nature Reserve, Tenterden and Hastings Visit the historic houses, gardens and vineyards the area has to offer Great for walkers with easy access to local footpaths

Superhost

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, 421 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 favorite

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

4.92 out of 5 average rating, 317 reviews

Charming Little Worker’s Cottage

Built in the 1860’s this little rustic one bedroom workers cottage is a place to relax and a base for exploring. Situated in 0re, nearby paths lead to the beautiful Hastings Country Park Nature Reserve with its coastal country walks, ancient woodlands and dramatic clifftop sea-views. Set back from the road, along a terrace of small cottages, this is a place for quiet and bird song.

Guest favorite

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, 224 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.