Holiday houses in Winchelsea

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Top-rated holiday rentals in Winchelsea

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Guest favourite
The exterior of the cottage features a welcoming entrance with double doors framed by white flowers. A slate roof complements the whitewashed walls, while a stone pathway leads to the front door, surrounded by neatly trimmed greenery.
Cottage in Pett Level
4.94 out of 5 average rating, 193 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.

Top Guest favourite
Cottage in East Sussex
4.99 out of 5 average rating, 119 reviews

Birch Cottage, Rye, Coastline Views & Hot Tub

My place is close to Rye & the beaches of Camber Sands & Winchelsea. October-March late checkout on Sundays (4pm), midweek stays enjoy a discounted rate. It is a perfect spot to unwind combining beautiful countryside with sea air and amazing views from the private garden and terrace of the English Channel. Birch Cottage in the grounds of the main house once owned by the comedian & author Spike Milligan. Newly renovated to a high modern standard, with a brand new kitchen & two new bathrooms.

Top Guest favourite
The oak-framed cottage is set against a clear blue sky, showcasing solar panels on the sloped roof. A spacious lawn surrounds the building, and wooden patio furniture is visible on the sunlit terrace, inviting outdoor relaxation.
Home in Heathfield
4.9 out of 5 average rating, 372 reviews

Jacks Cottage -

A beautiful oak framed building with great views of the south downs. Accommodation comprising of a comfortable lounge with TV and wifi and log burner. The kitchen is well equipped with a dishwasher, oven and microwave. One double bedroom downstairs with en suite shower room. Upstairs there is a mezzanine with two single beds and a sitting area above the lounge area with a bathroom with free standing bath. The outside space is a south facing patio with table and chairs and a BBQ is available.

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
4.97 out of 5 average rating, 355 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.

Top Guest favourite
Cottage in Winchelsea Beach
4.95 out of 5 average rating, 118 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
A self-built studio cabin is presented in a peaceful outdoor setting, featuring a red roof and dark wooden exterior. A small patio area with two chairs is visible at the front. Nearby, a wooden storage unit adds functionality to the space.
Cabin in Rye Harbour
4.96 out of 5 average rating, 152 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
An expansive balcony with wooden decking is showcased, featuring a long table and lounge chairs. The view encompasses lush greenery and the shimmering expanse of Rye Bay in the distance, while the coastline is visible beneath a clear sky.
Home in East Sussex
4.97 out of 5 average rating, 101 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.

Guest favourite
The exterior of Hop Pickers Retreat is showcased, featuring a wooden facade with large glass windows. A spacious deck area includes seating and a woodfired hot tub, surrounded by greenery. The structure blends modern and natural elements, providing a serene outdoor space.
Cabin in East Sussex
4.95 out of 5 average rating, 203 reviews

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.

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, 357 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
Home in Rye
4.99 out of 5 average rating, 159 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.

Superhost
The entrance features a charming wooden door painted in a soft green hue, leading to a cozy interior. A pair of wellington boots and a flower pot with pink blooms sit at the doorstep, alongside a rustic stool. Coats hang from hooks nearby, enhancing the welcoming atmosphere.
Bungalow in Winchelsea Beach
4.9 out of 5 average rating, 468 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 favourite
The spacious kitchen and dining area features light wood paneling and oak flooring. The well-equipped kitchen showcases soft blue cabinetry, an electric oven, and a gas stove. A circular dining table with wooden chairs is placed near a window that provides natural light.
Home in Winchelsea Beach
4.87 out of 5 average rating, 226 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.

Popular amenities for Winchelsea holiday rentals

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