
Vacation rentals in Winchelsea
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Top-rated vacation rentals in Winchelsea
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Wooded Bubble tent
Located on a 120 acre farm. The ultimate star gazing pad. The unusual lodging is fully equipped to help you enjoy a excellent and original night. A cosy bed, a toilet, shower, clean towels and a thousand stars over you. Lay in bed turn off the lamps and start counting. Enjoy a relaxing wood burning hot tub with a glass of prosecco, inhale a breath of fresh air and lay back and enjoy the views of the North downs. Tap onto my profile picture see my other bubbles. Not suitable for under 4 years.
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The Lodge at Maidlands Oast - Nr Rye, East Sussex
Maidlands Lodge is a detached converted barn boasting stunning uninterrupted far reaching views across the Tillingham Valley. It provides guests the ultimate luxury retreat and romantic getaway for two nestled in the heart of the breathtaking rolling East Sussex countryside . This light and airy property is presented to the highest of standards throughout providing top quality linens and bedding as standard. The underfloor heating also ensures a cosy retreat throughout the winter months.
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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.
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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.
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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
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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.
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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.
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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.
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Beach Boutique
Welcome to Beach Boutique — a lovely, dog-friendly little hideaway a 5-minute wander from Camber Sands’ dunes (and all that big-sky beach magic). It’s a cosy 2-bed that’s spot-on for couples or small families, with a properly equipped kitchen, enclosed garden for pups, Sky TV, superfast WiFi, and a crackling fireplace for post-beach cosiness. It’s the kind of place that works just as well for windswept winter weekends as it does for sunny summer breaks.
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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.
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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.
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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.
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Popular amenities for Winchelsea vacation rentals
Other great vacation rentals in Winchelsea

Beachfront views of Rye Bay, with EV charger.
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Cosy cottage in Rye Harbour
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Old Smock Windmill in rural Kent
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The Stables, Rye
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The Oaks. Beautiful Scandi style cabin on stilts
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Charming Church View Cottage with Garden
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Stylish house on Winchelsea beach, East Sussex
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Matchbox is a delightful pet-friendly cottage
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Destinations to explore
- Brighton Seafront
- Le Touquet
- Greenwich Park
- Botany Bay
- Royal Wharf
- Dreamland Margate
- Leeds Castle
- Streatham Common
- Cuckmere Haven
- Plage de Calais
- Romney Marsh
- Saint Andrew's Lakes
- Brighton Palace Pier
- Glyndebourne
- Adventure Island
- Worthing Pier
- Rochester Cathedral
- Eastbourne Beach
- Blackheath
- Golf Du Touquet
- Folkestone Beach
- Wissant L'opale
- Peckham Rye
- Ashdown Forest





