
Cottage holiday rentals in Winchelsea
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Winchelsea
Guests agree: these cottages are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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.

The Long Stable: Rural haven, spacious, fast Wifi
Stylishly fitted and eco-friendly, our detached, self-contained cottage is in a very rural location. There are no other holiday cottages on the farm. Situated in the High Weald Area of Outstanding Natural Beauty, on a sheep farm of 23 acres (which you are free to roam), this is a real get-away-from-it-all location. One of the most peaceful and relaxing places you will ever stay. With underfloor heating and a wood-burning stove you will be cosy whatever the weather.

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.

Ticehurst Home with a view
Cottage This two bedroomed cottage is set down a quiet lane adjacent to Bewl Water, which is the largest stretch of open water in the South East. The 800 acre site is set in an Area of Outstanding Natural Beauty, in the heart of the High Weald and very popular with walkers, cyclists and fishermen.

Charming cottage with minstrels gallery in 7 acres
A cosy, light and spacious traditional oak-framed building with a minstrels' gallery and a full height living area. Standing in seven acres of private grounds, on the path of an ancient but now forgotten travellers' way, Whistlers is surrounded by meadows, orchards and woodland walks.
Popular amenities for cottage rentals in Winchelsea
Cottage rentals with a hot tub

Evegate Manor Barn

'Oak Lodge' Littlebourne, Canterbury (hot tub)

Plantagenet: A Historic Country Cottage with Pool

Cosy Thatched Cottage in Kent | Hot Tub | Sleeps 6

Blackthorn is a luxurious, rural retreat for two.

Daweswood - Luxury countryside cottage, lake & tub

Beautiful Cottage Retreat + Hot Tub + Spa

Cottage in the Wood, Detling
Pet-friendly cottage rentals

Setts Wood Cottage, Tenterden

Converted barn with garden & private sun terrace

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

Hastings Old Town cottage with sea views

Modern, comfortable, level entry, dogs welcome

The Annex at Buttons Farm

Delightful pet-friendly oast with private garden

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

Crown Stables. A romantic retreat in historic Rye.

See Britain's Beautiful Countryside from this Chic Cottage

Cosy 2 Bedroom Cottage In Rye

The Paper Mill Stables

Cottage with a view.

Wild hideaway near Lewes

The Cabin - a little ranch house. A peaceful haven

Tranquil Hastings Hideaway: Escape to Our Cottage
Destinations to explore
- Le Touquet
- ExCeL London
- Brighton Seafront
- Dreamland Margate
- Nausicaá National Sea Center
- Greenwich Park
- Royal Wharf
- Leeds Castle
- Plage de Calais
- Peckham Rye
- Worthing Pier
- Cuckmere Haven
- Glyndebourne
- Golf Du Touquet
- Wissant L'opale
- Romney Marsh
- Adventure Island
- Brighton Palace Pier
- University of Kent
- Streatham Common
- Rochester Cathedral
- Folkestone Beach
- Dover Castle
- Eastbourne Beach





