Vacation rentals in Winchelsea

Matchbox is a delightful pet-friendly cottage

Matchbox is a beautiful listed cottage in the heart of Winchelsea, overlooking the stunning church. The whole cottage has been finished to a high standard. A fully equipped galley kitchen, open plan lounge/diner and separate TV snug. Upstairs you have two king size bedrooms with views towards the church and each with their own bath/shower room. There is a small, fully fenced outdoor area that is secure for dogs and available for guests to use. ONLY ONE WELL BEHAVED DOG ALLOWED FOR A PET FEE

Stylish, quiet bungalow in Winchelsea Beach

A renovated bungalow nestled in a quiet cul-de-sac in a peaceful seaside village. On the verge of a bustling nature reserve and a short walk or bike ride to the beautiful coastline, this home has everything you need to explore the local area. The shingle beach is glorious any time of year and quieter than other local beaches. There are easy walks to Pett Level, Rye or to inland villages (and wonderful local pubs). Being close to Pett Pools and Rye Harbour, it is ideal for birdwatchers.

Pebbles - a calm and peaceful retreat near the sea

Pebbles is a place to relax and unwind, situated in a private annexe at our home in Pett Level. You’ll be only five minutes walk from an amazing beach. Surrounded by beautiful 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. Pebbles has a lounge overlooking the garden, double bedroom, wet room and a fully fitted kitchen. The garden is secluded and peaceful . The beautiful town of Rye is 5 miles away.

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.

Beachfront views of Rye Bay, with EV charger.

Beach-front views of Rye Bay, a spacious modern house set above the beach on a private lane. Its four bedrooms enjoy sea views and there's room on the balcony to relax in the morning sun. The second floor Belvedere (lookout) gives extensive views across Rye bay to English Channel. A great base for exploring Hastings, Rye and East Sussex, or simply going to the beach. There are 32 steps up to the house. 7kW EV charger, bring your type 2 cable (pay online per kWh). Pet free.

14th-Century House in Rye's Historic Citadel

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 are round the cobbly corner.

Cosy cottage in Rye Harbour

Welcome to our idyllic sea-side cottage in Rye Harbour, just down the road from a cosy pub, a village store, and a nature reserve. The nature reserve is ideal for walks and birdwatching, and is home to the Discovery Centre where you can grab a coffee and learn about the area. There are lots of pubs, cafes, restaurants & a winery in Rye town, 5 minutes away by car. The house is also conveniently located for day trips to Winchelsea and Camber Sands.

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.

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.

The Yard Rye

The Yard is a two-bed interior-designed cottage in the citadel of the beautiful Cinque Port town of Rye. It is situated down a cobbled passageway next to a pretty tea room. PLEASE NOTE – The property can sleep up to two adults in the master bedroom and one child in the single, with a pull-out camp bed if needed for an extra child. We also have a travel cot for an infant. Please be aware we have a steep staircase.

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.

The Stables, Rye

A characterful and charming property in the Ancient Town and Cinque Port of Rye. Recently renovated 'The Stables' is believed to have originally formed a part of Rye's original town wall and benefits from a wealth of period charm. Located at the bottom of Mermaid street and opposite the bustling Strand, you will find antique shops scattered amongst restaurants a stones throw away!