Winchelsea cottages

Holiday cottages and self-catering accommodation in Winchelsea

Winchelsea is a delightful little town, allegedly the smallest in England and with its very own mayor! Once a major hub of the medieval wine trade, it was moved up to the hills after a flood caused the original town of Old Winchelsea to be lost to the sea back in the 13th century. More like a village, it perches above the lower seaside part of Winchelsea Beach and is the home of Spike Milligans’s final resting place. Equidistant between Hastings and Rye, it is a lovely place to base yourself as you explore the Sussex and Kent countryside.

Winchelsea itself is something very different to other towns. Tiny and perched on a hilltop, it has blocks of houses in squares, all surrounding a spectacular church which was once an abbey; you can still see some of the remnants to this day. Historical tours of the church and town are much recommended and be sure to visit the original stone-vaulted wine cellars. Two huge stone gates are situated at both entrances in Winchelsea – you can imagine horses with carriages thundering through them centuries ago!

Hastings is only five miles away and is a hive of activity, with old antique shops and pubs sitting alongside typical seaside attractions. Five miles further afield is Battle, famous for its abbey where William the Conqueror defeated King Harold, and its lovely shops and tearooms.

Find your perfect place to stay on the Easter Sussex coast by browsing our selection of Winchelsea holiday cottages above for even more inspiration.