Vacation rentals in Winchelsea Beach

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Top-rated vacation rentals in Winchelsea Beach

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Guest favorite

Condo in East Sussex

4.91 out of 5 average rating, 167 reviews

Rye High Street, delightful flat in centre of Rye

We are located on the High Street in the heart of medieval Rye, perfect for exploring this beautiful historic town. Our flat is on the 2nd floor, the stairs are winding so not recommended if you have mobility issues. Open plan kitchen & living area, separate bedroom with king size bed, shower room, Please Note * The shower cubicle is small but works well! 3 minutes walk from station, pubs, restaurants & car parks, we recommend the Cattle Market car park, Rope Walk TN31 7NA £2.50 for 24 hours.

Jun 27 – Jul 4

G$29,814 GYD per night

Guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 205 reviews

Pebbles - calm and relaxing by the sea

Pebbles is a private annexe at our home in Pett Level, a haven of quiet and calmness. We are 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.

Oct 15 – 22

G$29,596 GYD per night

Guest favorite

Cottage in East Sussex

4.99 out of 5 average rating, 103 reviews

Driftwood is a 2 minute stroll to Pett Level Beach

A perfect blend of stunning coast and countryside on the doorstep. Driftwood is a beautifully renovated three bedroom beach house that’s two minutes stroll from the beach and surrounded by miles of beautiful countryside including spectacular cliff top walks. Historic Rye and Camber Sands are a short drive away. The house is unassuming from the outside, and once you’re inside it feels light, warm and welcoming with a Scandi vibe. All rooms are on one spacious floor. Dogs are very welcome.

May 31 – Jun 7

G$80,987 GYD per night

Guest favorite

Cottage in Peasmarsh

4.92 out of 5 average rating, 117 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.

Jun 19 – 26

G$34,394 GYD per night

Guest favorite

Guesthouse in East Sussex

4.99 out of 5 average rating, 319 reviews

The Annex

A two bedroom self-contained cottage set in the East Sussex countryside, with views of the Fairlight Hall Estate and the English Channel. On a clear day you can see as far as Dungeness and the inter-lying beaches. Situated between the historic old fishing port of Hastings and the fortified hilltop town of Rye, on the A259. The Annex is next door to a family home within their established garden, to which guests have access. The nearest railway stations are Battle or Hastings.

Dec 6 – 13

G$29,094 GYD per night

Guest favorite

Cottage in Icklesham

4.88 out of 5 average rating, 172 reviews

Rural Holiday Cottage

Tucked away in an unspoilt part of East Sussex on a traditional working sheep farm, our idyllic self-catering cottage is set in an area of outstanding natural beauty with stunning views across the valley & a sea vista. Contemporary high end self catering holiday cottage. Dogs and horses are welcome. We are very close to beaches at Winchelsea and Camber. The village pub is a 5 minute walk and there are many other lovely pubs a short drive away.

Oct 3 – 10

G$27,058 GYD per night

Guest favorite

Cottage in East Sussex

4.99 out of 5 average rating, 241 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.

Oct 11 – 18

G$31,601 GYD per night

Guest favorite

Condo in East Sussex

4.94 out of 5 average rating, 188 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 in the oldest part of Rye. 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 2 floors! These are also super steep so please be careful with children. A 10 minute walk from Rye station.

Jun 30 – Jul 5

G$31,793 GYD per night

Guest favorite

Cottage in East Sussex

4.84 out of 5 average rating, 206 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.

Feb 28 – Mar 7

G$25,668 GYD per night

Guest favorite

Apartment in East Sussex

4.93 out of 5 average rating, 180 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

Sep 23 – 30

G$21,688 GYD per night

Guest favorite

Condo in East Sussex

4.94 out of 5 average rating, 233 reviews

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.

Nov 17 – 24

G$24,399 GYD per night

Guest favorite

Bungalow in Winchelsea Beach

4.91 out of 5 average rating, 337 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.

Oct 27 – Nov 3

G$38,291 GYD per night