Winchelsea Holiday Rentals

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Our top choices for Winchelsea holiday rentals

Cottage in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
9.8 out of 10, Exceptional, (10 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 NZ$659
includes taxes & fees
5 Feb - 6 Feb
1 bedroom accommodation in Winchelsea Beach, near Rye

Holiday Home in Winchelsea

Sparrows Den Lodge
3.5 star property
The price is NZ$902
includes taxes & fees
16 Jan - 17 Jan
Sparrows Den Lodge

Apartment in Winchelsea Beach

White Haven - with 2 double rooms
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 NZ$580
includes taxes & fees
17 Jan - 18 Jan
White Haven - with 2 double rooms
2.0 star property
9.4 out of 10, Exceptional, (30 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is NZ$338
includes taxes & fees
19 Jan - 20 Jan
Pinewood Camping Pods - At Port Lympne Reserve
10.0 out of 10, Exceptional, (1 review)
"Nice and Memorable stay "
United Kingdom
Kishore S.
The price is NZ$580
includes taxes & fees
13 Jan - 14 Jan
Victory - idyllic holiday home in 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 NZ$610
includes taxes & fees
13 Jan - 14 Jan
Rhodown - sun on the terrace all round

Aparthotel in Eastbourne

Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (95 reviews)
"Great stay"
United Kingdom
George
Osborne Apartments

Apartment in Bexhill-on-Sea

Bexlet
2.0 star property
8.6 out of 10, Excellent, (50 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is NZ$185
includes taxes & fees
19 Jan - 20 Jan
Bexlet
2.0 star property
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 NZ$281
includes taxes & fees
9 Feb - 10 Feb
Calm Private Annex Ideal to Work, Rest & Explore
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 NZ$271
includes taxes & fees
13 Jan - 14 Jan
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
10.0 out of 10, Exceptional, (3 reviews)
"Had a great mini break with my grandchildren. Weather was ‘wall to wall’ sunshine. Accommodation was excellent had everything you needed. The beach was just across the road from the camp site. Chalet situated in a quieter part of the site and had a big grass area just outside"
United Kingdom
Cheryl M.
The price is NZ$298
includes taxes & fees
13 Jan - 14 Jan
Our cosy chalet is just a 5-minute stroll from the golden sands of Camber Beach.
10.0 out of 10, Exceptional, (6 reviews)
"Perfect location. Perfectly comfortable."
United Kingdom
alex
The price is NZ$269
includes taxes & fees
14 Jan - 15 Jan
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
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 NZ$366
includes taxes & fees
13 Jan - 14 Jan
2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.

Apartment in Dymchurch

Ocean Sea View Suite
10.0 out of 10, Exceptional, (4 reviews)
"Our stay at the Ocean Sea View Suite was lovely. We had a great experience from the booking to the checkout. The property is well kept and clean. Amazing location with shops, food and entertainment options just on the door step. The cherry on the cake was the beautiful sandy beach. "
United Kingdom
Djanicie M.
The price is NZ$438
includes taxes & fees
18 Jan - 19 Jan
Ocean Sea View Suite
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 NZ$610
includes taxes & fees
13 Jan - 14 Jan
Beach Lodge - 5 minute walk to the sandy beach

Cottage in Cowbeech, near Hailsham

1 bedroom accommodation in Cowbeech, near Hailsham
10.0 out of 10, Exceptional, (2 reviews)
"Cedar Lodge was exactly what we were looking for and we felt at home as soon as we arrived. The accommodation was clean, cosy and very well equipped and the hosts Caroline and Neil were very welcoming. The comments in the visitors book showed that many people have visited here several times and feel it’s the best holiday home they have stayed in. The location is very quiet and the view from the deck is beautiful. I wouldn’t hesitate to stay here again if we are visiting the area."
United States
Carolyn Armstrong
The price is NZ$355
includes taxes & fees
13 Jan - 14 Jan
1 bedroom accommodation in Cowbeech, near Hailsham

Apartment in Dymchurch

Beachfront Bliss Apartment
8.0 out of 10, Very good, (1 review)
"Apartment photos completely accurate,very comfortable, very clean.Only negative was shortage of storage space in bedrooms. Joshua was excellent in communicating with us."
United Kingdom
Sheila W.
The price is NZ$438
includes taxes & fees
19 Jan - 20 Jan
Beachfront Bliss Apartment
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 NZ$507
includes taxes & fees
13 Jan - 14 Jan
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

Holiday Home in Hastings

Family Caravan Rental 2 bed Caravan
2.0 star property
The price is NZ$265
includes taxes & fees
7 Feb - 8 Feb
Family Caravan Rental 2 bed Caravan

Holiday Home in Eastbourne City Centre

"The Gateway to Birling Gap + Seven Sisters- RB&B Living
2.0 star property
The price is NZ$145
includes taxes & fees
21 Jan - 22 Jan
"The Gateway to Birling Gap + Seven Sisters- RB&B Living
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

Find out more about Winchelsea

Everything you need to know about Winchelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchelsea holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchelsea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchelsea holiday rentals we have selected for you start as low as NZ$299 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchelsea rentals

At Expedia, we put the best Winchelsea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchelsea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchelsea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchelsea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Matchbox: This highly rated holiday home rental in Winchelsea has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach 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.