
Photo by Simon Carey (CC BY-SA)
Winchelsea cottages
We found 216 cottages — enter your dates for availability
Explore Winchelsea cottage rentals
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Sleeps 2 · 1 bedroom · 2 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Loke Cottage – Winchelsea Town – Near Rye
Sleeps 5 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
4 Landgate Cottage sleeps 4 in Winchelsea near Rye, East Sussex
Sleeps 4 · 2 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The Cot - a holiday let that sleeps 6 guests in 3 bedrooms
Sleeps 6 · 3 bedrooms · 2 bathrooms
The Gazebo in Winchelsea
Sleeps 2 · 1 bedroom · 1 bathroom
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Sleeps 4 · 2 bedrooms
9.69.6 out of 10
Exceptionalexceptional
176 reviews(176 reviews)
Top rated cottage rentals - Winchelsea
Lovely property and great value
1010 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
Lovely place
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
Lovely weekend break
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Property for a break
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Had a great weekend
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Excellent Experience!
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Getaway
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Fantastic stay!
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
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- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any cottage rentals in Winchelsea?
Enjoy a cosy, homelike ambience and more room to move compared to a hotel when you choose one of the 216 cottage rentals in Winchelsea. Base yourself in this neighbourhood and you’ll be within a short distance of top-rated attractions like Rye Harbour Nature Reserve, Pett Level Beach and Winchelsea Beach.
How much does it cost to stay in a cottage rental in Winchelsea?
Upscale or budget, in a busy tourist area or a little way out, high season or shoulder season — these factors and more will determine how much your cottage rental in Winchelsea will cost. How long you choose to stay can also affect the overall price. Some properties offer discounts for guests staying longer, so keep your eyes peeled for special deals.
When is the best time to rent a cottage in Winchelsea?
It all comes down to how much you want to spend, what kind of weather you like and if you prefer the buzz of peak season or a more chill vibe. Located in East Sussex, July is when most people visit Winchelsea, when the average temperatures range between 14ºC (57ºF) and 20ºC (68ºF). Browse the availability of our cottage rentals at different times of the year and then book your favourite.
Where can I rent a Winchelsea holiday cottage with great views?
Use the “Location” filter to find a cottage rental with the views you’re seeking. Start by entering the dates you want to book your accommodation in Winchelsea, then narrow your search based on the type of area you’d rather stay in.
Does Winchelsea have any lakeside cottages?
Lovely views of glistening water, the serenity of nature and outdoor recreation are just a few of the things to enjoy in one of Vrbo’s lakeside cottage rentals. Try our “Location” filter and click on “Lake” to find out if there are any cosy retreats in Winchelsea overlooking the water.
What are the top things to do in Winchelsea?
Keep your group busy at Rye Harbour Nature Reserve, Pett Level Beach and Winchelsea Beach. These are only some of the family-friendly things to do you’ll find around Winchelsea. Whatever your idea of the perfect family getaway, our cottage rentals have the space you need to unwind and connect.
Why should I book my holiday cottage with Vrbo?
No sharing your space, no uncomfortable encounters with strangers. When you pick a Vrbo cottage rental, you get the entire place to yourself. Need to alter or cancel your plans? Our flexible cancellation policies let you book your cottage with peace of mind. Plus, thanks to our One Key™ rewards programme, you’ll be able to earn and use OneKeyCash™* on all eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.