Holiday houses in Winchelsea Beach

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Top-rated holiday rentals in Winchelsea Beach

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Guest favourite
Barn in Brede Rye
4.95 out of 5 average rating, 181 reviews

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.

Top Guest favourite
A comfortable lounge area features a mix of seating, including a light-colored sofa and an orange accent chair. The space is complemented by a wooden coffee table, a large area rug, and natural light from the window. A wall-mounted TV and decorative shelves add character.
Home in Winchelsea
4.98 out of 5 average rating, 95 reviews

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.

Top Guest favourite
A serene beach scene features a sandy shore with smooth rocks scattered throughout. The clear blue sky reflects over calm waters, and a cliff with greenery rises majestically in the background, offering a tranquil view of the coastline.
Cottage in East Sussex
4.98 out of 5 average rating, 364 reviews

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.

Guest favourite
A spacious living area features large windows that frame captivating sea views. A wooden dining table is set between the windows, accompanied by two chairs. A plant is placed on each side of the room, and simple furnishings are styled for a relaxed atmosphere.
Apartment in Hastings
4.99 out of 5 average rating, 165 reviews

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

Guest favourite
A charming outdoor seating area features a light blue table and two matching chairs placed on a gravel surface. Surrounded by greenery and colorful flowers, the entrance to the cozy cottage is visible in the background, framed by a wooden trellis overhead.
Cottage in Winchelsea Beach
4.93 out of 5 average rating, 122 reviews

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.

Top Guest favourite
The exterior of the studio cabin showcases a black wooden facade with a red roof. White-framed windows are positioned symmetrically on either side of the entrance. A small patio area is visible, featuring two garden chairs and a table, with a grassy area surrounding the cabin.
Cabin in Rye Harbour
4.96 out of 5 average rating, 161 reviews

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.

Top Guest favourite
The charming exterior of the seaside cottage is showcased, featuring a light green front door framed by blooming pink flowers and lush greenery. A wooden bench is positioned on a path leading to the entrance, set against a clear blue sky.
Home in Rye Harbour
4.94 out of 5 average rating, 382 reviews

Charming, Cosy Cottage in Rye Harbour

Light and airy seaside cottage with lots of character. Built in around 1900, it was originally home to one of the local coastguards who were stationed in the village. Cosy and comfortable sitting room. Open plan kitchen diner opening in to the sunny sheltered garden. The kitchen is well equipped, with microwave, electric oven, washer dryer and dishwasher. There is a double bedroom and a single room with bunk beds. The family bathroom is downstairs,and we have an upstairs toilet.

Top Guest favourite
A two-story cottage is framed by lush greenery and flowering shrubs. Two white deck chairs are positioned on the lawn, accompanied by a small outdoor dining set. Large windows adorn the home, enhancing natural light. A Juliet balcony overlooks the garden.
Guesthouse in East Sussex
4.99 out of 5 average rating, 449 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.

Top Guest favourite
A panoramic view showcases the coastline of Rye Bay under a clear blue sky. The image captures the serene sea and sandy beach lined with sparse vegetation, while the distant shoreline is visible. The landscaped area and nearby structures provide context to the scenic setting.
Home in East Sussex
4.97 out of 5 average rating, 105 reviews

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.

Top Guest favourite
A charming view of Mermaid Street is captured, showcasing an array of historic buildings with black and white exteriors. Cobblestone paths wind through the scene, accompanied by neatly trimmed hedges and planters. A decorative sign hangs above, adding character to the quaint street.
Condo in Rye
4.95 out of 5 average rating, 370 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.

Top Guest favourite
A charming bedroom is highlighted by a striped headboard adorned with decorative pillows. An accented wall in warm tones complements framed artwork above the bed. A small tray table holds a vase with fresh flowers, adding a touch of color and elegance to the space.
Home in Rye
4.99 out of 5 average rating, 169 reviews

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.

Guest favourite
Home in East Sussex
4.95 out of 5 average rating, 41 reviews

Stylish house on Winchelsea beach, East Sussex

Sitting on the shores of Winchelsea Beach is Cloudbreak – a new contemporary build, with stunning views of the sea and easy access to the beach that is directly on the doorstep of this modern property, built beside the bike path and walkway along the beach. It is a short drive from the medieval town of Rye with all its history – Cloudbreak is perfectly situated to explore the surrounding area.

Popular amenities for Winchelsea Beach holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. East Sussex
  5. Winchelsea Beach