Winchelsea Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Winchelsea holiday rentals

Terrace/patio

1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (11 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
The price is HK$2,998
HK$2,998 total
includes taxes & fees
5 Feb - 6 Feb
1 bedroom accommodation in Winchelsea Beach, near Rye
Interior

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is HK$3,361
HK$4,034 total
includes taxes & fees
31 Jan - 1 Feb
Sparrows Den Lodge
Exterior

White Haven - with 2 double rooms

White Haven - with 2 double rooms
Winchelsea Beach
2.0 out of 10, (1 review)
"Check in was easy and location was good, thise are the only positives. The property is extremely dated and dirty. The furnishings in communal areas were torn, threadbare, stained, dirty and smelly. The carpets were dirty, covered in dog and human hair. There was mould above the shower and dirt and mould under the sink. The areas around the toilets were soiled with rusted old urine splashes. There was mould on one of the bedroom walls.The kitchen cupboard fascias were peeling and the handles all...
United Kingdom
Emma V.
The price is HK$753
HK$2,626 total
includes taxes & fees
24 Jan - 25 Jan
White Haven - with 2 double rooms
Room

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
The price is HK$727
HK$872 total
includes taxes & fees
30 Jan - 31 Jan
Chestnut Meadow Camping
TV

Victory - idyllic holiday home in Hastings

Victory - idyllic holiday home in Hastings
Hastings
10.0 out of 10, Exceptional, (1 review)
"Nice and Memorable stay "
United Kingdom
Kishore S.
The price is HK$753
HK$2,584 total
includes taxes & fees
16 Feb - 17 Feb
Victory - idyllic holiday home in Hastings
Living area

Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (31 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is HK$1,235
HK$1,483 total
includes taxes & fees
26 Jan - 27 Jan
Pinewood Camping Pods - At Port Lympne Reserve
1 bedroom, free WiFi, bed sheets

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Bexhill
10.0 out of 10, Exceptional, (6 reviews)
"Perfect location. Perfectly comfortable."
United Kingdom
alex
The price is HK$1,036
HK$1,203 total
includes taxes & fees
23 Jan - 24 Jan
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Free WiFi

Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
9.0 out of 10, Wonderful, (96 reviews)
"Great stay"
United Kingdom
George
Osborne Apartments
Garden

Calm Private Annex Ideal to Work, Rest & Explore

Calm Private Annex Ideal to Work, Rest & Explore
2.0 star property
Ashford
10.0 out of 10, Exceptional, (1 review)
"One night stay to visit local family. Very welcoming, met on arrival. Coldest night of the year so far and it was warm, cosy & comfortable. Owners live next door, attached house, easy parking, easy to find. Will possibly be return during 2026, central location for all our needs."
United Kingdom
Steve
The price is HK$729
HK$874 total
includes taxes & fees
9 Feb - 10 Feb
Calm Private Annex Ideal to Work, Rest & Explore
Miscellaneous

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (50 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is HK$689
HK$826 total
includes taxes & fees
5 Feb - 6 Feb
Bexlet
1 bedroom, iron/ironing board, free WiFi, bed sheets

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (11 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
The price is HK$942
HK$1,214 total
includes taxes & fees
8 Feb - 9 Feb
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
Exterior

Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite

Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite
Flimwell, Wadhurst
9.4 out of 10, Exceptional, (3 reviews)
"Our trip to the Shepherds Hut was nothing short of idyllic! Our host Jay was so helpful and kind, even going so far as to give us a lift to Tunbridge Wells when our pre-booked taxi didn't show up. The outdoor kitchen was so easy to use, and made an al fresco breakfast very lovely. We took full advantage of the firepit - logs and kindling provided for us - as well as the lovely walks nearby. I would recommend to anyone looking to get away for a bit of peace and beauty!"
United Kingdom
Josi K.
The price is HK$792
HK$960 total
includes taxes & fees
26 Jan - 27 Jan
Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite
TV

Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.2 out of 10, Wonderful, (5 reviews)
"Lovely peaceful setting and the caravan had everything you would need and bonus being so close to Hastings"
United Kingdom
William E.
The price is HK$879
HK$2,762 total
includes taxes & fees
24 Jan - 25 Jan
Rhodown - sun on the terrace all round
Living area

Gun Hill Cottage

Gun Hill Cottage
3.5 star property
Heathfield
10.0 out of 10, Exceptional, (2 reviews)
"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"
United Kingdom
Thomas
The price is HK$6,402
HK$7,683 total
includes taxes & fees
30 Jan - 31 Jan
Gun Hill Cottage
2 bedrooms, iron/ironing board, travel cot, WiFi

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
Mersham
10.0 out of 10, Exceptional, (3 reviews)
"WE had an excellent stay with our two young grandchildren. It was perfectly located as we had visited Chatham historic dockyard and spending the next day at Tenterden heritage railway. So much so the youngest wanted to stay an extra night! The description is spot on, Our host extremely helpful with local knowledge. Highly recommend "
United Kingdom
Malcolm T.
The price is HK$1,132
HK$1,593 total
includes taxes & fees
2 Feb - 3 Feb
2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
1 bedroom, WiFi

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
10.0 out of 10, Exceptional, (3 reviews)
"We had a delightful stay in the Garden Room. So peaceful and spacious. The bi-folding doors to the garden were a perfect touch - along with the comfortable bed and great coffee machine. Highly recommend!"
United States
Anonymous traveller
The price is HK$2,192
HK$2,192 total
includes taxes & fees
2 Feb - 3 Feb
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
TV

Beach Lodge - 5 minute walk to the sandy beach

Beach Lodge - 5 minute walk to the sandy beach
Camber
8.8 out of 10, Excellent, (10 reviews)
"Fantastic lodge near the beach on a great location in the park. Highly recommend "
United Kingdom
Laura J.
The price is HK$879
HK$2,762 total
includes taxes & fees
25 Jan - 26 Jan
Beach Lodge - 5 minute walk to the sandy beach
1 bedroom, iron/ironing board, free WiFi, bed sheets

Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
Hythe
8.0 out of 10, Very good, (3 reviews)
"The closeness to the High St. meant it was easy to walk to find something to eat/drink. The host was very helpful."
United Kingdom
David
The price is HK$644
HK$773 total
includes taxes & fees
5 Feb - 6 Feb
Pet Friendly Private Cabin Town Eurotunnel Beach
Exterior

Family Caravan Rental 2 bed Caravan

Family Caravan Rental 2 bed Caravan
2.0 star property
Hastings
The price is HK$607
HK$1,201 total
includes taxes & fees
6 Feb - 7 Feb
Family Caravan Rental 2 bed Caravan
Property grounds

Calm Private Apartment in Ashford – Ideal to Work, Rest & Explore

Calm Private Apartment in Ashford – Ideal to Work, Rest & Explore
2.0 star property
Ashford
The price is HK$804
HK$804 total
includes taxes & fees
23 Jan - 24 Jan
Calm Private Apartment in Ashford – Ideal to Work, Rest & Explore
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.
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Top Winchelsea Hotel Reviews

Cavendish Hotel

Cavendish Hotel

10/10 Excellent
"Is a little tired but really clean and nothing is to much trouble "
Michael 2-night trip
Posted 2 days ago
Cavendish Hotel

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

Frequently asked questions

Can I find holiday rentals in Winchelsea?

Yes, there are holiday rentals close to the most popular sights in Winchelsea, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What are some of the best holiday rentals that Winchelsea has to offer?

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly: This holiday home rental outside of Winchelsea offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Winchelsea?

With 6 Expedia holiday rentals, you're guaranteed 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 holiday rental in Winchelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchelsea. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.