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Holiday Rentals in Winchelsea

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Holiday Rentals in Winchelsea

Grogu's Rest - 2 bedrooms with decking sleeps 6
8.8 out of 10, Excellent, (8)
"great stay again"
United Kingdom
lindsay r.
The price is €265
includes taxes & fees
16 Nov - 17 Nov
Grogu's Rest - 2 bedrooms with decking sleeps 6
1 bedroom accommodation in Winchelsea Beach, near Rye
9.8 out of 10, Exceptional, (9)
"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 €344
includes taxes & fees
6 Nov - 7 Nov
1 bedroom accommodation in Winchelsea Beach, near Rye
Sparrows Den Lodge
3.5 star property
The price is €420
includes taxes & fees
9 Nov - 10 Nov
Sparrows Den Lodge
White Haven - with 2 double rooms
2.0 out of 10, (1)
"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 €251
includes taxes & fees
16 Nov - 17 Nov
White Haven - with 2 double rooms
Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.4 out of 10, Exceptional, (29)
"We had a lovely stay here, introducing our little boy to camping for the first time. It was a lovely and cosy pod for the 3 of us and it was amazing being right next to the lions. We loved toasting marshmallows by the fire pits & all the on site restaurants were lovely and delicious food. We had a great time. "
United Kingdom
Ann
The price is €163
includes taxes & fees
5 Nov - 6 Nov
Pinewood Camping Pods - At Port Lympne Reserve
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
2.0 star property
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
9.4 out of 10, Exceptional, (3)
"Excellent"
United Kingdom
Melanie G.
The price is €188
includes taxes & fees
9 Nov - 10 Nov
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (87)
"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."
United Kingdom
Lucy
Osborne Apartments
Extraordinary Huts
3.0 star property
9.6 out of 10, Exceptional, (40)
"Really unique stay, lovely views."
United Kingdom
Louise
The price is €162
includes taxes & fees
19 Nov - 20 Nov
Extraordinary Huts
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
10.0 out of 10, Exceptional, (11)
"Host was so friendly upon arrival and made check in very easy. The property and parking were easy to find. The property itself was very clean and cosy and had everything you could possibly need. The bed was so comfortable and we loved the woodburner and shower. We LOVED LOVED LOVED waking up to the sights and sounds of the animals in the morning and being able to get up close and feed them made the stay extra special. We cannot wait to return!"
United Kingdom
Alannah M.
The price is €136
includes taxes & fees
5 Nov - 6 Nov
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
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"
United Kingdom
Ann
The price is €87
includes taxes & fees
17 Nov - 18 Nov
Bexlet
Victory - idyllic holiday home in Hastings
10.0 out of 10, Exceptional, (1)
"Nice and Memorable stay "
United Kingdom
Kishore S.
The price is €251
includes taxes & fees
16 Nov - 17 Nov
Victory - idyllic holiday home in Hastings
Peaceful Retreat, Sovereign Harbour, Eastbourne - FREE WELCOME PACK
10.0 out of 10, Exceptional, (50)
"Very clean apartment, welcome package, good space and a nice garden. Great for a little stay by the sea."
United Kingdom
Xan
The price is €197
includes taxes & fees
9 Nov - 10 Nov
Peaceful Retreat, Sovereign Harbour, Eastbourne - FREE WELCOME PACK
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
10.0 out of 10, Exceptional, (1)
"We had a great time here for my boyfriends birthday. The hot tub is lovely and the surrounding area beautiful with lots of amenities. Feels very private even though you're next to 3 other huts. I'd really recommend it and will be coming back to stay"
United States
Anonymous traveller
The price is €232
includes taxes & fees
18 Nov - 19 Nov
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
The Writers Retreat- Hastings
10.0 out of 10, Exceptional, (3)
"This was a very lovey place for a stay vacation cottage was very clean and well equip with everything we needs even tennis rackets it was quite and peaceful Beatiful park and very close to town and beach would definitely stay there again"
United Kingdom
Clarissa I.
The price is €253
includes taxes & fees
5 Nov - 6 Nov
The Writers Retreat- Hastings
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
10.0 out of 10, Exceptional, (5)
"Immaculately clean, modern, bright apartment. Mark was a very friendly host, communication was simple and easy. Perfectly located, close to the action, yet very peaceful. Would highly recommended. Front room cafe very good for breakfast. "
United Kingdom
Joanne W.
The price is €135
includes taxes & fees
16 Nov - 17 Nov
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Rhodown - sun on the terrace all round
9.2 out of 10, Wonderful, (5)
"Wasn’t sure when we arrived as outside of caravan could have done with a jet wash. Inside though was lovely we couldn’t fault it at all. Some reviews have mentioned the garden not being secure but we had no problems at all. The park itself is very very hilly but beautifully kept. The club house was very clean and all the staff we met were very friendly. One small niggle - we didn’t realise it had limited Wi-Fi and would have been happy to pay a charge for extra Wi-Fi. Overall a lovely time was...
United States
Judith R.
The price is €265
includes taxes & fees
16 Nov - 17 Nov
Rhodown - sun on the terrace all round
The Boathouse
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is €463
includes taxes & fees
14 Nov - 15 Nov
The Boathouse
1-bedroom Apartment Sleeps 4, Parking
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is €150
includes taxes & fees
14 Nov - 15 Nov
1-bedroom Apartment Sleeps 4, Parking
Ocean Sea View Suite
10.0 out of 10, Exceptional, (4)
"Check in easy, location fabulous. Bed comfortable - we slept really well - must be the sea air! The extra touches for our furry friend were spot on - doggy bowls and doggy treats were most welcome. Only very small gripe - we could’ve done with bigger towels but overall what a lovely break we had. "
United Kingdom
Debra F.
The price is €238
includes taxes & fees
16 Nov - 17 Nov
Ocean Sea View Suite
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, apart-hotels, 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 €87 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?

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winchelsea?

With 5 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.