Cottage vacation rentals in Winchelsea

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Top-rated cottage rentals in Winchelsea

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Guest favorite

Cottage in Pett Level

4.96 out of 5 average rating, 109 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.

Aug 2 – 9

G$79,461 GYD per night

Guest favorite

Cottage in Icklesham

4.97 out of 5 average rating, 195 reviews

Blackthorn is a luxurious, rural retreat for two.

Blackthorn is a luxurious retreat for two. Attached to the owner's home, and situated on the edge of Icklesham village, the property lies halfway between the ancient towns of Rye and Hastings. There is a distant view of the sea, and the garden is surrounded by beautiful AONB countryside. The cottage has a private, south facing verandah, and guests are welcome to use the heated, indoor swimming pool and outdoor hot tub throughout their stay but exclusively between the hours of 8.00am and 8.00pm.

Jan 31 – Feb 7

G$41,345 GYD per night

Guest favorite

Cottage in Rye

4.97 out of 5 average rating, 278 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 two single sofa-beds. 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.

Mar 6 – 13

G$44,172 GYD per night

Guest favorite

Cottage in Sandhurst

4.96 out of 5 average rating, 275 reviews

The Cabin - a little ranch house. A peaceful haven

Located in the High Weald area of Kent which is an AONB, The Cabin at Valley View Farm is set in its own space amongst 16 acres of wood and grazing. It used to be an old hop pickers mobile home but has been lovingly restored to a modern, well presented “mini” haven. A fully self-contained cabin with open plan lounge/dining/kitchen area, UK king size bed in bedroom and a shower room and toilet. Ideal for a couple or two singles as a Z-bed can be provided. Private outside veranda with a fire pit

Dec 27 – Jan 3

G$18,278 GYD per night

Guest favorite

Cottage in Sandhurst

5.0 out of 5 average rating, 324 reviews

Cosy Cottage with Woodburner & Countryside Views.

Cowbeach Cottage is Grade II listed and has been lovingly restored to a high standard. It features a wealth of old oak beams and an inglenook fireplace with a cosy wood burning stove. It is tastefully decorated throughout to provide a relaxing space. The bespoke oak staircase leads to a beautiful vaulted bedroom with views across the Kent countryside. The cottage benefits from a private south facing garden and patio. It is ideally situated to explore the many National Trust properties close by.

Mar 15 – 22

G$29,815 GYD per night

Guest favorite

Cottage in East Sussex

4.97 out of 5 average rating, 209 reviews

Pebbles - calm and relaxing by the sea

Pebbles is a private annexe at our home in Pett Level, a haven of quiet and calmness. We are only five minutes walk from an amazing beach. Surrounded by fabulous 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. There is a bright lounge with french doors overlooking the garden, wet room, double bedroom and fully fitted kitchen. The garden is secluded and peaceful . The beautiful town of Rye is 5 miles away.

Dec 9 – 16

G$30,992 GYD per night

Guest favorite

Cottage in East Sussex

4.99 out of 5 average rating, 107 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.

Sep 11 – 18

G$81,764 GYD per night

Guest favorite

Cottage in Peasmarsh

4.92 out of 5 average rating, 118 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.

Sep 23 – 30

G$37,121 GYD per night

Guest favorite

Cottage in Camber Sands

4.93 out of 5 average rating, 116 reviews

Beautiful Camber Sands home away from home

Sea Holly Cottage, on the award-winning White Sand development is a chic child and dog friendly haven with easy access to the stunning Camber beach and surrounding area of natural beauty. The cottage is spacious & well decorated, with high-quality mattresses, luxurious linen, black out blinds, fast wi-fi & a sun trap garden. A huge, comfy sofa; family bathroom and downstairs toilet; a kitchen well stocked for cooking up a storm; local artists featured throughout. A true home from home.

Sep 29 – Oct 6

G$30,480 GYD per night

Guest favorite

Cottage in East Sussex

4.99 out of 5 average rating, 242 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 is open plan with large Smart TV & free Netflix. 2 bathrooms. Free high speed WiFi throughout. Sunny conservatory, private garden with sun loungers & BBQ. Amazing coastal and countryside walks right from the doorstep.

Dec 13 – 20

G$28,986 GYD per night

Guest favorite

Cottage in Playden, Rye

4.88 out of 5 average rating, 154 reviews

Characterful cottage for two on quiet farm lane

Willow cottage is a one bedroom detached home on a quiet farm lane in Playden, 2 mins drive from Rye, the historic cinque port town. The perfect cottage for a couple (plus baby) to relax in. There are plenty of country walks direct from the cottage and Camber Sands and Winchelsea beaches a 10mins drive away. There is a dedicated parking space outside. The owners are next door to give you local recommendations if required.

Oct 6 – 13

G$33,670 GYD per night

Guest favorite

Cottage in East Sussex

4.84 out of 5 average rating, 209 reviews

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.

Feb 17 – 24

G$24,168 GYD per night