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Winchelsea Vacation Rentals

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Vacation Rentals in Winchelsea

Close to the beach and to historic Rye - delightful 3 bed Cottage & garden
Exterior
Close to the beach and to historic Rye - delightful 3 bed Cottage & garden
9.8 out of 10, Exceptional, (93)
"Very comfortable, clean and cozy cottage. Close to the beach, beautiful walks. Shop close by, including a yummy fish and chip shop. The cottage is well equipped with everything you might need. Also a lovely garden to sit in / eat in. Will definitely return. Thank you so much"
Close to the beach and to historic Rye - delightful 3 bed Cottage & garden
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Terrace/patio
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
10.0 out of 10, Exceptional, (21)
"Lovely place! Lovely people! Definitely recommend"
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Vive Hotel
Exterior
Vive Hotel
4.0 star property
7.8 out of 10, Good, (52)
"Central location, new hotel modern decor. Great place to day "
The price is CA $189
CA $227 total
includes taxes & fees
Jun 13 - Jun 14
Vive Hotel
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Cosy 3-bed Caravan,combe Haven st Leonards on sea
Cabin | Private kitchen
Cosy 3-bed Caravan,combe Haven st Leonards on sea
3.0 star property
Cosy 3-bed Caravan,combe Haven st Leonards on sea
Osborne Apartments
Deluxe Apartment
Osborne Apartments
2.5 star property
9.2 out of 10, Wonderful, (40)
"The reception team were very professional and friendly."
The price is CA $157
CA $189 total
includes taxes & fees
Jun 13 - Jun 14
Osborne Apartments
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, (11)
"This was the best experience ever I booked this for my husbands birthday he loved it so much he said it was like staying in the jungle hearing the lions roar it’s magical the pinewood lodge was lovely and cosy we loved our stay thank you so much and it the price was well worth it I would highly recommend."
The price is CA $246
CA $296 total
includes taxes & fees
Jun 18 - Jun 19
Pinewood Camping Pods - At Port Lympne Reserve
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town
Fridge, microwave, oven, stovetop
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town
9.2 out of 10, Wonderful, (104)
"The flat was in a great location and Martyn the host was very helpful. It’s a large, light and airy space with 2 good sized bedrooms and a huge lounge/diner (though we tended to eat in the kitchen). The decor is very neutral & everywhere is very clean. We would definitely stay again."
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town
Superb medieval house with spacious private garden in the centre of Rye
Interior
Superb medieval house with spacious private garden in the centre of Rye
10.0 out of 10, Exceptional, (77)
"This is a lovely house right in the centre of Rye, in walking distance from everywhere. Despite this it is quiet. The house is beautiful and has everything you need."
Superb medieval house with spacious private garden in the centre of Rye
Character Country Retreat with no contact check in/out, in historic 1066 country
Property grounds
Character Country Retreat with no contact check in/out, in historic 1066 country
9.8 out of 10, Exceptional, (194)
"It was the 2nd time we have stayed there and we had a lovely relaxing time"
Character Country Retreat with no contact check in/out, in historic 1066 country
Extraordinary Huts
The Hide Out | Living room
Extraordinary Huts
3.0 star property
9.8 out of 10, Exceptional, (25)
"Loved the hut, enjoyed our stay. I brought a 3 course meal with me. So no need to eat out! Lovely and cosy. I would have liked a small saucepan to do porrige in morning. We managed with a big one!! I also wasnt good with lighting the gas rings. I would prefer a long lighter . And no hooks for towels when wet out of shower. In bedroom there were a few cobwebs and spiders in nooks and crannies. Whilst not scared, I felt these had been on ceiling and edges for some time. However bed very cosy....
The price is CA $265
CA $265 total
includes taxes & fees
Jun 6 - Jun 7
Extraordinary Huts
Grace Apartments - Living Rock
Miscellaneous
Grace Apartments - Living Rock
3.5 star property
6.8 out of 10, (3)
"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
T's Beach House Beautiful sea views and direct beach access
Beach
T's Beach House Beautiful sea views and direct beach access
10.0 out of 10, Exceptional, (49)
"A deceptively spacious accommodation which easily slept 9 adults. The kitchen was well stocked with the usual items and smoothly led onto the dining area and garden area. The living room and bedrooms were really tastefully decorated and again, spacious. Would I use this accommodation again? Yes, it met our needs, nicely located for a walking weekend and our host was very helpful in answering all our questions"
T's Beach House Beautiful sea views and direct beach access
Bexlet
Miscellaneous
Bexlet
2.0 star property
9.0 out of 10, Wonderful, (36)
"Great accommodation with everything I needed. Clean and comfortable. Really close to the beach - a minute’s walk - but tucked away a bit behind shops. Would recommend."
The price is CA $103
CA $124 total
includes taxes & fees
Jun 17 - Jun 18
Bexlet
Premium holiday home
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Premium holiday home
9.2 out of 10, Wonderful, (38)
"Lovely place for our short weekend trip. Property was well kept, clean, well stocked and roomy. Overall park was nice but not many facilities for young children (the play park could be much better) however the pool was great baby pool well heated! Great location close to amenities and Hastings town. Owner responsive and helpful. Thank you for a great stay"
Premium holiday home
Converted stable in secluded rural setting.
Outdoor dining
Converted stable in secluded rural setting.
10.0 out of 10, Exceptional, (121)
"Lovely area, plenty of wildlife to see. Bigger than it looked in the photos. Named the woodpeckers Ronnie and Reggie as they chased the other birds off. 😁 Will definitely look to stay again when back in this area."
Converted stable in secluded rural setting.
A pretty 4* detached rural holiday cottage in the heart of the Kent countryside
Exterior
A pretty 4* detached rural holiday cottage in the heart of the Kent countryside
10.0 out of 10, Exceptional, (69)
"The let was clinically clean and poorly designed ithe a ground floor shower room / loo accessible through the Kitchen area and lounge and with no upstairs ablution arrangement. The motor exit is EXTREMELY dangerous to the unwary and I would not return for this reason alone"
A pretty 4* detached rural holiday cottage in the heart of the Kent countryside
Caravan Nearby Hastings, Coghurst Hall Park
Chalet | Pool
Caravan Nearby Hastings, Coghurst Hall Park
3.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely caravan with cute little sheltered garden off the veranda."
The price is CA $248
CA $336 total
includes taxes & fees
Jun 19 - Jun 20
Caravan Nearby Hastings, Coghurst Hall Park
Outstanding luxury beachfront holiday experience with hot tub
Property grounds
Outstanding luxury beachfront holiday experience with hot tub
10.0 out of 10, Exceptional, (97)
"Our stay at the Beach House was perfect……from the location to all the little extras and finer details to make it feel like home from home. We were a party of 9 celebrating a friends 50th birthday, but the house felt spacious with plenty of outdoor space & furniture for us all to enjoy the fabulous weather we had. The hot tub was an added bonus as were the views from the master bedroom. We’ll definitely be back!"
Outstanding luxury beachfront holiday experience with hot tub
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Exterior
16th Century Cottage Situated Opposite The Medieval Landgate Arch
9.6 out of 10, Exceptional, (162)
"Our family of 4 plus woofer dog had a great time and Chesterfield cottage was great to base ourselves from. The courtyard was a little suntrap in the afternoons for the very rare times we actually stayed in the cottage during the day. Comfy and everything we needed - thank you again Richard for having us!"
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Boutique Nights Willow
Deluxe Studio Suite
Boutique Nights Willow
3.0 star property
9.0 out of 10, Wonderful, (2)
"Only internet don’t work properly but the room is the best you can have very happy "
Boutique Nights Willow
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See all available properties in Winchelsea
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.

Other types of properties in Winchelsea you may be interested in

Winchelsea Lodge
Luxury Suite, Ensuite, River View (Heron)
Winchelsea Lodge
3.0 star property
8.6 out of 10, Excellent, (237)
"The room was very clean, everything you needed was there, would highly recommend windchelsea lodge to stay at."
The price is CA $144
CA $173 total
includes taxes & fees
Jun 7 - Jun 8
Winchelsea Lodge
The Burlington Hotel
Superior Double Room, 1 Double Bed, Sea View
The Burlington Hotel
3.0 star property
7.6 out of 10, Good, (707)
"Centrally location "
The price is CA $58
CA $70 total
includes taxes & fees
Jun 16 - Jun 17
The Burlington Hotel
The View Hotel
Exterior
The View Hotel
3.0 star property
9.2 out of 10, Wonderful, (1003)
"We’ve stayed at the View Hotel many times in the past staff are very friendly and accommodating good hospitality and facilities."
The price is CA $122
CA $147 total
includes taxes & fees
Jun 9 - Jun 10
The View Hotel
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.

Everything you need to know about Winchelsea vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchelsea vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchelsea vacation rentals we have selected for you start as low as CA $103 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 vacation 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 vacation.

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 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.

What's the top vacation rental that Winchelsea has to offer?

Cosy 3-bed Caravan,combe Haven st Leonards on sea: This vacation home near Winchelsea offers a fireplace, a private yard, and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winchelsea?

With 7 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 Church of St Thomas a Becket 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.

Recent reviews of Winchelsea properties
Expedia verified reviews

The Lansdowne, Eastbourne

The Lansdowne, Eastbourne

5/5 Excellent
Lovely stay on the beachfront
"We had a great stay in the hotel (2 adults, 2 kids, 2 nights). Our room was bright and clean, and surprisingly spacious. Upon arrival, we noted that we were expecting an extra bed in our room; one was promptly sent up and made up. Breakfast was excellent. The hotel is 3-stars for a reason: it hasn't been refurbished in a long time, so if you're looking for examples of cutting edge design, you might try somewhere else (probably outside of Eastbourne?). But The Lansdowne is very well looked after by the staff, and this gives the hotel a lovely nostalgic feel. Whenever we're headed to Eastbourne again we'll try to stay there first."
A verified traveller stayed at The Lansdowne, Eastbourne
Posted 2 days ago
The Lansdowne, Eastbourne