Cottage holiday rentals in Winchelsea

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Top-rated cottage 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
The private garden features a well-maintained grassy area surrounded by trees. The cottage is visible with large glass doors leading to a terrace. Two lounge chairs are positioned on the patio, offering a spot to enjoy the outdoor scenery.
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.

Guest favourite
An aerial view captures the coastal cottage surrounded by a well-maintained garden, featuring a large patio with outdoor seating. The beach and ocean are visible in the background, while a clear blue sky completes the scene. The structure has a light blue exterior and is situated near a road.
Cottage in Rye
4.96 out of 5 average rating, 414 reviews

Mayfayre - 2 Bed Cottage Beside the Beach

This luxurious two bedroom cottage is right beside the sandy beach. There is a spacious open-plan lounge (inc wood-burner) and dining area. The two double bedrooms have built-in wardrobes on the ground floor and stairs to a mezzanine suitable for children with a tv and bean bags. The kitchen is fully equipped including a washer, drier, fridge freezer and all crockery and cutlery. The ground floor bathroom has bath (with shower), sink & WC. Outside is a large family garden, table & chairs.

Guest favourite
A copper-style bath is showcased against a dark wall, complemented by ambient lighting. Beside the tub, a standing champagne bucket is positioned next to two sparkling flutes, resting on a small wooden table adorned with decorative coasters.
Cottage in Sedlescombe
4.97 out of 5 average rating, 190 reviews

Cosy one bedroom Grade 2 listed Country Cottage.

A charming, Grade 2 listed country cottage, dating from the 1700’s. Located in the village of Sedlescombe, which retains its charm of an old English village, in an Area of Outstanding Natural Beauty. Recently renovated, the cottage has been refurbished to a high standard. With underfloor heating in the bespoke wet room & a magnificent copper style bath in the bedroom. Whilst downstairs the cosy sitting room benefits from a wood burning stove & the spacious kitchen leads to a courtyard garden.

Guest favourite
An open-plan dining and kitchen area features a wooden table set for four, with a basket of flowers as a centerpiece. A modern kitchen layout includes a stove and fridge, and a staircase leads to the upper level, showcasing industrial-style railings.
Cottage in Kent
4.91 out of 5 average rating, 164 reviews

Idyllic 2- Bedroom barn with amazing views

Spacious barn conversion with views of the countryside. The Barn is an ideal location to use as a base for visiting the many places of interest or for a relaxing holiday. There are many National Trust properties within a small radius together with historic gardens and local vineyards. Tenterden and Rye are a short drive and Camber Sands, with its sandy beach, is a must. There are a number of local pubs which serve food, The White Hart within a few minutes walk, and many others not far away.

Top guest favourite
The indoor swimming pool features clear, inviting water surrounded by lush greenery. Large windows allow natural light to fill the space, offering views of the private garden. Comfortable seating is positioned along the edges, creating a relaxing atmosphere for guests.
Cottage in East Sussex
4.98 out of 5 average rating, 304 reviews

Badgers Den - Covehurst Bay Holiday Cottage

Luxury self-catering holiday cottage in the countryside near Hastings. Heated indoor swimming pool, steam room, gym & outdoor hot tub. 2 bedrooms and 2 bathrooms, suitable for up to 4 people. Kitchen, dining & living room are open plan with a large Smart TV & free Netflix. Free high-speed WiFi throughout. Sunny conservatory, private garden with a deck & sun loungers. Glass-roofed veranda with gas BBQ and seating for socialising. Amazing coastal and countryside walks right from the doorstep.

Top guest favourite
A charming cottage displays a wooden shingle exterior with a distinctive green door. The two-story structure features multiple windows, inviting natural light. The well-maintained facade is complemented by a cobblestone pathway, reflecting the historic character of its surroundings.
Cottage in East Sussex
4.95 out of 5 average rating, 132 reviews

23 Tower St., Landgate Cottage, Rye

Landgate Cottage is ideally located, opposite the remaining 14th Century Landgate entrance to the old citadel in the heart of Rye. Everything is nearby, with shops, tea rooms, bistros, pubs, restaurants and the Kino Rye cinema also. There is fantastic access to coast and countryside. Close to car parks (£3.00 / 24 hrs), bus stops and Rye railway station (London St Pancras is an hour and 4 mins). Two double bedrooms, bath, shower, fully equipped kitchen and outside terrace with seating.

Top guest favourite
An outdoor patio area is illuminated by warm string lights, with a spacious wooden table at its center. Two comfortable white chairs are arranged around a fire pit, surrounded by landscaped greenery. Small plants and decorative elements are placed on the table, enhancing the inviting setting.
Cottage in East Sussex
4.98 out of 5 average rating, 159 reviews

Driftwood is a 2 minute stroll to Pett Level Beach

A perfect blend of stunning coast and countryside on the doorstep. Driftwood is a beautifully renovated three bedroom beach house that’s two minutes stroll from the beach and surrounded by miles of beautiful countryside including spectacular cliff top walks. Historic Rye and Camber Sands are a short drive away. The house is unassuming from the outside, and once you’re inside it feels light, warm and welcoming with a Scandi vibe. All rooms are on one spacious floor. Dogs are very welcome.

Guest favourite
A small wooden table is set outdoors, accompanied by two glasses, a bottle, and a vase with flowers. A nearby green apple rests on the table, while greenery and a tranquil water feature create a peaceful backdrop.
Cottage in Peasmarsh
4.9 out of 5 average rating, 196 reviews

Peace, Quiet, Cosy house with garden & log burner

Peaceful, with good views, great walks, 2 sitting rooms, big cosy log burning stove, big fluffy towels & dressing gowns, 600TC sheets, super comfy bed, plumped pillows, 2 big smart TVs, wifi & Sonos. Soak in a free-standing bath or big shower and stretch out on an enormous sofa and admire the view up the valley - You won't want to leave! If you do the Little House is well placed for pubs, beaches, vineyards, gardens, Rye and Hastings and many other treats only a walk or short drive away.

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, 354 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.

Guest favourite
Cottage in Camber
4.94 out of 5 average rating, 217 reviews

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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