Photo by John Scale

Holiday Rentals in Winchelsea

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winchelsea

Close to the beach and to historic Rye - delightful 3 bed Cottage & garden
9.8 out of 10, Exceptional, 93 reviews
"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.
10.0 out of 10, Exceptional, 21 reviews
"Lovely place! Lovely people! Definitely recommend"
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Vive Hotel
4.0 star property
8.0 out of 10, Very good, 55 reviews
"Probably the single cleanest place in hastings. Great room. all furniture and fittings brand new. Staff were very friendly. Well done Vive team."
The price is €138
includes taxes & fees
26 Jun - 27 Jun
Vive Hotel
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
2.5 star property
9.2 out of 10, Wonderful, 41 reviews
"The reception team were very professional and friendly."
The price is €403
includes taxes & fees
26 Jun - 27 Jun
Osborne Apartments
Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.2 out of 10, Wonderful, 12 reviews
"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 €223
includes taxes & fees
19 Jun - 20 Jun
Pinewood Camping Pods - At Port Lympne Reserve
Extraordinary Huts
3.0 star property
9.8 out of 10, Exceptional, 25 reviews
"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 €184
includes taxes & fees
25 Jun - 26 Jun
Extraordinary Huts
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town
9.2 out of 10, Wonderful, 105 reviews
"We really enjoyed our stay in Martyns lovely apartment in Hastings old town. It had everything we needed and was spacious and comfortable. It was close to all amenities and made a perfect base."
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town
Character Beamed Country Retreat with self check in/out in historic 1066 country
9.8 out of 10, Exceptional, 194 reviews
"It was the 2nd time we have stayed there and we had a lovely relaxing time"
Character Beamed Country Retreat with self check in/out in historic 1066 country
Superb medieval house with spacious private garden in the centre of Rye
10.0 out of 10, Exceptional, 78 reviews
"We stayed for three nights, and really enjoyed pottering round Rye and mornings on the beach. Robin Hill is a wonderful place to stay, a welcoming and comfortable family home. Communication was excellent, the house very clean, and it was so nice to stay somewhere with character and history in equal measure! Many thanks :)"
Superb medieval house with spacious private garden in the centre of Rye
Luxury Beachfront Two Bedroom Apartment with Sea Views and Free Private Parking
9.8 out of 10, Exceptional, 143 reviews
"We had a wonderful stay at this lovely apartment, the photos really do not do it justice!!! Brilliant location to the local restaurants at the harbour and the views to the sea were amazing and so relaxing. We would love to stay here again and we will definitely return. Lovely little stay."
Luxury Beachfront Two Bedroom Apartment with Sea Views and Free Private Parking
Premium holiday home
9.2 out of 10, Wonderful, 38 reviews
"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
Entire Beach House, beautiful sea views & direct beach access on the Kent coast
10.0 out of 10, Exceptional, 49 reviews
"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"
Entire Beach House, beautiful sea views & direct beach access on the Kent coast
Quaint Cottage in Rye
10.0 out of 10, Exceptional, 94 reviews
"The cottage is beautiful, attention to detail is perfect. From the milk tea coffee and biscuits left for us to all the products we would need for our stay.The beds were so comfy and the bsthroom is lovely.Home from home.Rye is an amazing town.We will definately be back nexy year."
Quaint Cottage in Rye
Caravan Nearby Hastings, Coghurst Hall Park
3.0 star property
10.0 out of 10, Exceptional, 2 reviews
"Lovely caravan with cute little sheltered garden off the veranda."
The price is €217
includes taxes & fees
20 Jun - 21 Jun
Caravan Nearby Hastings, Coghurst Hall Park
Outstanding luxury beachfront holiday experience with hot tub
10.0 out of 10, Exceptional, 98 reviews
"A fantastic house. A great location. A perfect holiday with family."
Outstanding luxury beachfront holiday experience with hot tub
Bexlet
2.0 star property
9.0 out of 10, Wonderful, 36 reviews
"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 €79
includes taxes & fees
30 Jun - 1 Jul
Bexlet
Boutique Nights Willow
3.0 star property
9.0 out of 10, Wonderful, 2 reviews
"Only internet don’t work properly but the room is the best you can have very happy "
Boutique Nights Willow
Coastguard Cottage With Sea Views
9.8 out of 10, Exceptional, 47 reviews
"We spent 3 nights in this lovely cottage within the country Park, the cottage is incredibly well equipped in the kitchen , the views are amazing, all the way along the coast, Pett levels, Rye, Camber sands, Dungeness and in one particularly clear night France! Karen responded to queries immediately and was an excellent host. I certainly recommend this cottage."
Coastguard Cottage With Sea Views
A pretty 4* detached rural holiday cottage in the heart of the Kent countryside
10.0 out of 10, Exceptional, 71 reviews
"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
Don't see what you're looking for?
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
3.0 star property
8.6 out of 10, Excellent, 237 reviews
"The room was very clean, everything you needed was there, would highly recommend windchelsea lodge to stay at."
The price is €92
includes taxes & fees
19 Jun - 20 Jun
Winchelsea Lodge
The Burlington Hotel
3.0 star property
7.6 out of 10, Good, 725 reviews
"All okay "
The price is €74
includes taxes & fees
19 Jun - 20 Jun
The Burlington Hotel
The View Hotel
3.0 star property
9.2 out of 10, Wonderful, 1,000 reviews
"Ideal location very nice hotel "
The price is €100
includes taxes & fees
7 Jul - 8 Jul
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 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 €79 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?

Cosy 3-bed Caravan,combe Haven st Leonards on sea: This holiday home rental outside of Winchelsea offers a fireplace, a private garden 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 that you can cook with friends or family.

How many holiday rentals are there in Winchelsea?

With 7 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 Church of St Thomas a Becket 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.

Recent reviews of Winchelsea properties
Expedia verified reviews