
Cottage holiday rentals in Winchelsea
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Top-rated cottage rentals in Winchelsea
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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.

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.

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.

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.

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.

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.

Willow Cottage, Hot tub & Coastline views, Rye
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. The perfect spot to unwind, beautiful countryside & sea air, amazing views from the private garden over English Channel. Tennis court in main gardens available for guest use. Willow Cottage is the wing to the main house once owned by the comedian & author Spike Milligan. Newly renovated & fully refurbished to a high modern standard.

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.

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.

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.

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.

Charming Little Worker’s Cottage
Built in the 1860’s this little rustic one bedroom workers cottage is a place to relax and a base for exploring. Situated in 0re, nearby paths lead to the beautiful Hastings Country Park Nature Reserve with its coastal country walks, ancient woodlands and dramatic clifftop sea-views. Set back from the road, along a terrace of small cottages, this is a place for quiet and bird song.
Popular amenities for cottage rentals in Winchelsea
Cottage rentals with a hot tub

The Granary, Organic Vineyard stay with Pool.

Evegate Manor Barn

1 Bed in Ashford (oc-82527)

Beautifully Restored Tudor Cottage + Loft Apartmnt

Henry-Oscar House

Cosy Thatched Cottage in Kent | Hot Tub | Sleeps 6

Blackthorn is a luxurious, rural retreat for two.

Badgers Den - Covehurst Bay Holiday Cottage
Pet-friendly cottage rentals

Converted barn with garden & private sun terrace

Countryside views/Dog friendly/secure garden

Hastings Old Town cottage with sea views

No.2 Shepherd’s Cottages - steps from Camber beach

Modern, comfortable, level entry, dogs welcome

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Period Cottage, Iden, Rye, East Sussex. Sleeps 6

The Piggery-country hideaway, amazing valley views
Private cottage rentals

Matchbox is a delightful pet-friendly cottage

See Britain's Beautiful Countryside from this Chic Cottage

The Paper Mill Stables

Rye, Coach House, Cadborough Farm,

Hastings…A Pretty 2 bedroomed cottage

Spacious 3 bed maisonette in Hastings Old Town

The Cabin - a little ranch house. A peaceful haven

Riverside Stable Cottage, Hunton Yalding Maidstone
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
- Wissant L'opale
- Romney Marsh
- Adventure Island
- Golf Du Touquet
- Brighton Palace Pier
- University of Kent
- Streatham Common
- Rochester Cathedral
- Folkestone Beach
- Eastbourne Beach
- Dover Castle





