Vacation rentals in Winchelsea

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.

4.97 out of 5 average rating, 297 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.

4.9 out of 5 average rating, 183 reviews

A stand-alone shepherd's hut is set in a wooded area, featuring a dark green exterior and large windows. A small wooden deck and two chairs are positioned outside, alongside a circular fire pit surrounded by grass. Leafy trees provide a natural backdrop.

Hut in Udimore

The Staying Inn

The Staying Inn is a stand-alone Shepards hut set in the woodland of the south east. In the beautiful countryside, just outside rye and a stones throw from the coast of East Kent including camber sands. The space includes, a double mezzanine bed, fully equipped kitchen, log burner, shower room and decking, and lots of other quirky features. 5 mins car/taxi ride from rye Station, 15mins drive to camber sands ,and only 56 mins train ride from St Pancras station London to rye on the high speed.

4.94 out of 5 average rating, 205 reviews

A bright seating area features two comfortable armchairs positioned to face large triangular windows. Lush greenery and trees are visible outside, enhancing the sense of tranquility. Soft wooden flooring adds warmth to the space, while potted plants contribute to the inviting atmosphere.

Barn in East Sussex

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.

4.98 out of 5 average rating, 175 reviews

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

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.

The indoor swimming pool features clear, inviting water surrounded by lush greenery. Large windows allow natural light to fill the space, offering views of the private garden. Comfortable seating is positioned along the edges, creating a relaxing atmosphere for guests.

4.97 out of 5 average rating, 277 reviews

Badgers Den - Covehurst Bay Holiday Cottage

Luxury self-catering holiday cottage in the countryside near Hastings. Heated indoor swimming pool, steam room, gym & outdoor hot tub. 2 bedrooms and 2 bathrooms, suitable for up to 4 people. Kitchen, dining & living room is open plan with large Smart TV & free Netflix. 2 bathrooms. Free high speed WiFi throughout. Sunny conservatory, private garden with sun loungers & BBQ. Amazing coastal and countryside walks right from the doorstep.

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.

4.81 out of 5 average rating, 297 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.

4.94 out of 5 average rating, 178 reviews

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

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.

4.95 out of 5 average rating, 352 reviews

A stylish lounge bedroom features a king size bed adorned with a floral patterned duvet and plush pillows. A navy throw blanket is neatly placed at the foot of the bed. The room's walls are painted in a deep blue, and a wall clock is visible.

Condo in East Sussex

Beautiful boutique studio flat in town centre

Enjoy a stylish experience at this centrally-located place. This newly finished studio flat with fully furnished kitchen and dining area is in the centre of Medieval Rye, making it the perfect base to explore the historic Sussex south coast. This is a new property for us, however we are established hosts with super host status. Please do message if you have any questions. We’d love to hear from you.

Bungalow in Winchelsea Beach

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.

4.9 out of 5 average rating, 417 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.

4.86 out of 5 average rating, 220 reviews

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

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.

4.95 out of 5 average rating, 113 reviews

The exterior of the studio cabin showcases a black wooden facade with a red roof. White-framed windows are positioned symmetrically on either side of the entrance. A small patio area is visible, featuring two garden chairs and a table, with a grassy area surrounding the cabin.

Cabin in Rye Harbour

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)

The exterior of Dot Cottage features a charming bay window adorned with white lace curtains. A white door with a brass knocker sits beside it. Vibrant flowers bloom in soft pinks and purples, complementing the rustic brick façade.