Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

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Guest favorite

Guesthouse in Icklesham

4.87 out of 5 average rating, 105 reviews

Parsonage Barn Annex

Get the most from country relaxation at this lovely Barn annex placed right on the 1066 country walk route. The Parsonage Barn annex studio is a lovely 1 bedroom with its own private entrance from a very spacious garden. Situated in Icklesham right across from horse stables housing some beautiful pedigree horses in the heart of the farm valleys, just a few miles from Rye, the beautiful beaches of Camber Sands & Hastings, with a lovely 18th century pub 'The Queen's Head' 5 minutes down the road.

Jul 14 – 21

ﺩ.ﺇ476 per night

Guest favorite

Hut in Udimore

4.88 out of 5 average rating, 118 reviews

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.

Dec 9 – 16

ﺩ.ﺇ601 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

ﺩ.ﺇ520 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

ﺩ.ﺇ512 per night

Superhost

Guest suite in Broadoak Rye

4.85 out of 5 average rating, 368 reviews

Lantern Cottage Garden Studio

Lantern Cottage Garden Studio is a picturesque studio with its own private entrance. Situated in the High Weald, Broadoak Brede is in an area of outstanding natural beauty, surrounded by stunning woodland and only four miles from the historic Cinque Port town of Rye. Just a short drive away are the spectacular beaches of Camber Sands, Winchelsea Beach and Hastings. Other places of interest nearby are Battle ( the 1066 battle field), Camber castle and the stunning Bodiam castle.

Jun 4 – 11

ﺩ.ﺇ306 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

ﺩ.ﺇ526 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

ﺩ.ﺇ556 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

ﺩ.ﺇ559 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

ﺩ.ﺇ446 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

ﺩ.ﺇ381 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

ﺩ.ﺇ429 per night

Guest favorite

Bungalow in Winchelsea Beach

4.91 out of 5 average rating, 336 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

ﺩ.ﺇ673 per night