
Holiday houses in Winchelsea
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Top-rated holiday rentals in Winchelsea
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The Playhouse | Sleeps 2 | Rye | East Sussex
This unique property sits behind one of Rye's most iconic High Street shops. Tucked behind the main drag this architecturally important building has been completely restored and renovated. Offering a truly spectacular bolt hole from the demands of modern life but with all the mod cons. The Playhouse (one bedroom) is home to the quirky finds of its delightful owners, with an eye for colour, modern comforts, mixed in with playful vintage signs it creates a fabulous spot from which to explore.

Beach house in Dungeness
Beautiful Dungeness house right on the beach with ever changing views of the sea all year round. The house incorporates an original train carriage and the living space is open plan. The well equipped kitchen includes a generous dining table and chairs, which also looks out across the beach. There are two double bedrooms within the carriage as well as a shower room. An ideal place to explore Dungeness as well as discovering the wider area including Rye, Folkestone and the Romney Marsh.

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.

Escape to the Sea
Gorgeous, spacious, south-facing flat with stunning sea views, original features, and high ceilings. The sunrises/sets and moon reflections are breathtaking! In between St Leonards on Sea and Hastings, and 30 seconds to the beach! The bedroom has a king size bed and the living room a double sofabed. Bedding is cotton/linen washed with non toxic products. Flat is on the 3rd floor but not that many stairs and as such, sea views far from the madding crowd! There is free parking nearby

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.

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) There is also a seating area at the bottom of the garden. A sun umbrella when sitting outside is available for your use also.

Relaxing Luxury Retreat
Hop Pickers Retreat is found in the heart of an Area of Outstanding Natural Beauty (AONB) on the Kent and East Sussex border. Located on an farm you are surrounded by wildlife, birdsong, mooing cows, stunning views and in the summertime the sound of a combine, combining the crops in the surrounding fields. It is the ideal place to turn off that phone and unwind with your glass of your favourite tipple in the woodfired hot tub underneath the big starry sky.

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.

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.

Silverwood Studio Countryside Getaway
Escape to the countryside at Silverwood Studio, based on a farm in the most stunning location in Kent. We have recently renovated this barn to a high standard, complete with a log burner, kitchenette and a large picture window looking over the most fantastic view. It is located in a truly beautiful setting, in the middle of the English countryside, perfect for a romantic getaway or peaceful retreat.

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.

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.
Popular amenities for Winchelsea holiday rentals
Other great holiday rentals in Winchelsea

Luxurious retreat on Rye High Street

Chic Cottage in Centre of Historic Rye

Pelsham Farm Bungalow

Beachfront Bliss at Laughing Water

Summer vibes with the vine’s

Cottage in Rye, East Sussex

Channel View, Dungeness

The Oaks. Beautiful Scandi style cabin on stilts
Destinations to explore
- Le Touquet
- ExCeL London
- Brighton Seafront
- Dreamland Margate
- Nausicaá National Sea Center
- Greenwich Park
- Royal Wharf
- Leeds Castle
- Peckham Rye
- Plage de Calais
- Worthing Pier
- Cuckmere Haven
- Glyndebourne
- Romney Marsh
- Wissant L'opale
- Adventure Island
- Golf Du Touquet
- Brighton Palace Pier
- University of Kent
- Streatham Common
- Rochester Cathedral
- Folkestone Beach
- Eastbourne Beach
- Dover Castle





