Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

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Guest favorite

Cottage in Pett Level

4.93 out of 5 average rating, 134 reviews

Lovely Unique Beachfront Cottage

Stay right on wonderful Pett Level Beach in one of the original Coastguard's cottages, with direct access from the garden straight onto the sand. Recently modernised, the cottage has a super stylish open plan ground floor with kitchen, dining and living areas and wood burning stove. Upstairs there are two bedrooms: one has a double bed and sea view, the other can be made up either as a kingsize or as two single beds. Flexible space perfect for families or friends. A rare, stunning property.

Guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 248 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.

Guest favorite

Guesthouse in Icklesham

4.88 out of 5 average rating, 138 reviews

Peaceful Parsonage Barn Annex

Enjoy a peaceful stay at this lovely Barn annex placed right on the 1066 country walk route. The Parsonage Barn annex is a 1 bedroom with kitchen, bathroom and lounge with own private entrance from a very spacious garden. 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 min walk down the road.

Guest favorite

Guesthouse in East Sussex

4.99 out of 5 average rating, 361 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.

Guest favorite

Home in East Sussex

4.97 out of 5 average rating, 134 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.

Guest favorite

Condo in East Sussex

4.94 out of 5 average rating, 247 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

Cottage in East Sussex

4.82 out of 5 average rating, 254 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

Condo in East Sussex

4.95 out of 5 average rating, 293 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.

Guest favorite

Bungalow in Winchelsea Beach

4.91 out of 5 average rating, 370 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

Home in GB

4.86 out of 5 average rating, 212 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.

Guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 220 reviews

Perfect Isolation. Quaint Sussex Farm Cottage

Refurbished Spring ‘22 The perfect rural bolthole. Think The Holiday but you will need to supply Jude Law & Cameron Diaz. Waggoners is a private & quaint, cottage set in idyllic isolation, on a working farm, with luxurious handpicked furnishings. Outside- you are spoilt with a patio that bathes in sunshine all day. Please also see my other listings for further availability

Guest favorite

Guest suite in Icklesham

4.99 out of 5 average rating, 173 reviews

Valley View Cottage

We would like to welcome you to our detached cottage in the small village of Icklesham, between Hastings and Rye. With open countryside on the doorstep, there are plentiful walks including the 1066 Country Walk which runs long side the property. With comfortable space both inside and out, you can also just take it easy and enjoy the peace and tranquillity on offer.