Vacation rentals in Winchelsea

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Top-rated vacation rentals in Winchelsea

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Icklesham

4.89 out of 5 average rating, 101 reviews

Parsonage Barn Annex

Get the most from country relaxation at this lovely Barn annex placed right on the 1066 country walk route. The Parsonage Barn annex studio is a lovely 1 bedroom with its own private entrance from a very spacious garden. Situated in Icklesham right across from horse stables housing some beautiful pedigree horses in the heart of the farm valleys, just a few miles from Rye, the beautiful beaches of Camber Sands & Hastings, with a lovely 18th century pub 'The Queen's Head' 5 minutes down the road.

Jul 14 – 21

R2,490 ZAR per night
Guest favorite

Cottage in Pett Level

4.97 out of 5 average rating, 106 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.

Sep 2 – 9

R6,608 ZAR per night
Guest favorite

Guest suite in East Sussex

4.94 out of 5 average rating, 121 reviews

The French Shed

The French Shed is situated in a private area at the back of our cottage, it overlooks the fields and woods and Guestling church can be seen. Guests can relax and enjoy the seating area that is outside the shed , its a lovely place to sit watching the sun set enjoying a drink or having a BBQ. The Shed has been designed with the garden in mind , kitted out with lots of unique and interesting rustic finds a lot of which have come from France. It's a beautiful and unique place to relax and unwind.

Jan 23 – 30

R2,083 ZAR per night

Popular amenities for Winchelsea vacation rentals

Other great vacation rentals in Winchelsea

Superhost

Home in GB

4.86 out of 5 average rating, 200 reviews

Beautiful Beach House Winchelsea Beach East Sussex

Apr 11 – 18

R4,826 ZAR per night
Guest favorite

Bungalow in Rye Harbour

4.95 out of 5 average rating, 271 reviews

Coastal bolt-hole in Rye Harbour

Nov 21 – 28

R2,631 ZAR per night
Superhost

Hut in GB

4.93 out of 5 average rating, 441 reviews

The Hut

Nov 24 – Dec 1

R2,981 ZAR per night
Guest favorite

Barn in Rye Foreign

5.0 out of 5 average rating, 126 reviews

Little Mount @ Mount House, Rye

Sep 1 – 8

R2,951 ZAR per night
Superhost

Guest suite in Broadoak Rye

4.85 out of 5 average rating, 365 reviews

Lantern Cottage Garden Studio

Jun 24 – Jul 1

R1,602 ZAR per night
Guest favorite

Apartment in East Sussex

4.93 out of 5 average rating, 175 reviews

Hamiltons Nest

Aug 5 – 12

R1,943 ZAR per night
Guest favorite

Guesthouse in Rye

4.91 out of 5 average rating, 127 reviews

Amazing Views From Comfortable Cottage

Jul 15 – 22

R3,008 ZAR per night
Guest favorite

Windmill in Benenden

4.99 out of 5 average rating, 678 reviews

Old Smock Windmill in rural Kent

Feb 21 – 28

R5,846 ZAR per night
Guest favorite

Cottage in Sandhurst

5.0 out of 5 average rating, 315 reviews

Cosy Cottage with Woodburner & Countryside Views.

Feb 24 – Mar 3

R2,718 ZAR per night
Guest favorite

Cottage in Winchelsea Beach

4.93 out of 5 average rating, 54 reviews

Delightful 2 bedroom hideaway close to beach

Oct 4 – 11

R3,141 ZAR per night
Superhost

Cottage in East Sussex

4.82 out of 5 average rating, 85 reviews

Rosendal – Cosy Cottage for Countryside & Coast

Oct 20 – 27

R2,805 ZAR per night
Guest favorite

Cottage in East Sussex

4.84 out of 5 average rating, 19 reviews

4 Landgate Cottage sleeps 4 in Winchelsea, Nr Rye

Oct 8 – 15

R2,803 ZAR per night

Destinations to explore

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  3. England
  4. East Sussex
  5. Winchelsea