Photo by John Scale

Winchelsea Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 18 - Sep 19
Tomorrow
Sep 19 - Sep 20
This weekend
Sep 19 - Sep 21
Next weekend
Sep 26 - Sep 28

Vacation Rentals in Winchelsea

Osborne Apartments
1 bedroom, free WiFi

Osborne Apartments

2.5 star property
9.0 out of 10, Wonderful, (86)
"JUST FANTASTIC check in - Shree was SO helpful and showed us our room and how to check out. It was incredible service. Loved the room, the kitchen and it was just wonderful. Will be staying again soon."
Osborne Apartments
Vive Hotel
Exterior

Vive Hotel

4.0 star property
7.0 out of 10, Good, (84)
"The staff were amazing. "
Vive Hotel
Pinewood Camping Pods - At Port Lympne Reserve
Garden

Pinewood Camping Pods - At Port Lympne Reserve

2.0 star property
9.4 out of 10, Exceptional, (29)
"The staff are so friendly and helpfull and we all enjoyed out stay."
The price is P11,572
P13,886 total
includes taxes & fees
Oct 16 - Oct 17
Pinewood Camping Pods - At Port Lympne Reserve
Extraordinary Huts
Living room

Extraordinary Huts

3.0 star property
9.6 out of 10, Exceptional, (39)
"Beautiful views and great communication from the owner on how to find it and access your hut. We stayed in The Hive for one night and it was a little dusty, everything needed a deep clean. It didn’t ruin our trip, and would visit again in the hope this was a one off error."
The price is P10,991
P10,991 total
includes taxes & fees
Sep 22 - Sep 23
Extraordinary Huts
The Boathouse
Fridge, electric kettle, toaster, cookware/dishes/utensils

The Boathouse

3.0 star property
The price is P26,233
P31,480 total
includes taxes & fees
Oct 19 - Oct 20
The Boathouse
Bexlet
Miscellaneous

Bexlet

2.0 star property
8.6 out of 10, Excellent, (50)
"Easy to find on Sat Nav, parking nearby, very light, warm and comfortable, bed a little hard for us oldies. Overall great. Thank you"
The price is P4,910
P5,893 total
includes taxes & fees
Oct 19 - Oct 20
Bexlet
Tranquil Loft Apartment Overlooking Countryside
1 bedroom, free WiFi, bed sheets

Tranquil Loft Apartment Overlooking Countryside

3.0 star property
10.0 out of 10, Exceptional, (1)
Tranquil Loft Apartment Overlooking Countryside
Grace Apartments - Living Rock
Miscellaneous

Grace Apartments - Living Rock

3.5 star property
4.8 out of 10, (5)
"I needed immediate help when the sat sav dumped me nearby & my host talked me all the way to the front door which was a huge relief. The accommodation is dated but I knew that from the photos it was very clean though & i was surprised to find all the essentials had ben left. I wasn’t expecting that so had brought it all with me. The bed was very comfortable, the shower was lovely & the washing machine was handy. The area was very noisy though as it is right in town above a bar & I was there at...
Grace Apartments - Living Rock
Oastbrook Glamping
Exterior

Oastbrook Glamping

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
Oastbrook Glamping
Big2vacation2 Exclusive at new Beach Caravan Park
Property grounds

Big2vacation2 Exclusive at new Beach Caravan Park

3.0 star property
The price is P13,633
P16,360 total
includes taxes & fees
Oct 19 - Oct 20
Big2vacation2 Exclusive at new Beach Caravan Park
Big2vacation Exclusive Camber Sands Holiday Park
Children's area

Big2vacation Exclusive Camber Sands Holiday Park

3.0 star property
The price is P11,611
P13,934 total
includes taxes & fees
Sep 19 - Sep 20
Big2vacation Exclusive Camber Sands Holiday Park
Humphries Cross Apartments
Beach

Humphries Cross Apartments

3.0 star property
9.8 out of 10, Exceptional, (27)
"Lovely accommodation. Relaxing stay. "
Humphries Cross Apartments
Lovely 1 Bedroom Ground Floor Apartment max 4 per
Living area

Lovely 1 Bedroom Ground Floor Apartment max 4 per

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is P8,521
P10,225 total
includes taxes & fees
Sep 28 - Sep 29
Lovely 1 Bedroom Ground Floor Apartment max 4 per
Suspire House -sleeps6-garden-bbq-coastal Retreat
Private kitchen

Suspire House -sleeps6-garden-bbq-coastal Retreat

2.5 star property
The price is P11,010
P16,934 total
includes taxes & fees
Sep 28 - Sep 29
Suspire House -sleeps6-garden-bbq-coastal Retreat
Gun Hill Cottage
Interior

Gun Hill Cottage

3.5 star property
10.0 out of 10, Exceptional, (2)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
The price is P45,358
P54,430 total
includes taxes & fees
Oct 19 - Oct 20
Gun Hill Cottage
3 Elm Court
Living area

3 Elm Court

3.0 star property
The price is P23,648
P28,378 total
includes taxes & fees
Sep 28 - Sep 29
3 Elm Court
Oastbrook Estate Vineyard
Exterior

Oastbrook Estate Vineyard

3.5 star property
10.0 out of 10, Exceptional, (1)
"The property and setting are up there with the best we’ve ever stayed in. There’s loads to do locally and the host will help with this, or you can just relax in the house and grounds. A wonderful experiwnce!!!"
Oastbrook Estate Vineyard
Lilyrose Cottage
Property grounds

Lilyrose Cottage

3.0 star property
10.0 out of 10, Exceptional, (1)
"All very good. However too many disabled parking spaces meaning too few for others"
The price is P27,331
P32,798 total
includes taxes & fees
Oct 19 - Oct 20
Lilyrose Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchelsea Hotel Reviews

The View Hotel

The View Hotel

10/10 Excellent
"We have just enjoyed a lovely 5 night stay in a room with a side sea view balcony looking down to the pier. The hotel facilities were very good and the staff exceptional and so attentive to customers needs. We definitely intend to stay again in the future as it was perfect for our stay and a brilliant location. "
Chris 5-night trip
Posted 1 day ago
The View Hotel

Find out more about Winchelsea

Find out more about Winchelsea

Search for holiday rentals in Winchelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchelsea using one of the methods below:

  • View our selection of featured holiday rentals in Winchelsea
  • Use the map to find apartments and other holiday homes in the Winchelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchelsea while they last

Look no further and take a look at our great range of rental properties in Winchelsea!

Frequently asked questions

Can I find vacation rentals in Winchelsea?

Yes, we have vacation rentals near well known local attractions in Winchelsea, or you can select a more secluded option if you're looking for relaxation. Our travelers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

How many vacation rentals are there in Winchelsea?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Winchelsea stay.

What’s there to see and do in Winchelsea?

Winchelsea Beach and Pett Level Beach are a couple of lovely local spots to get outside and enjoy nature. High Weald and St. Thomas the Martyr are other places to visit while you're in town.

What’s a vacation rental in Winchelsea like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchelsea. Vacation rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.