Winchelsea Vacation Rentals from ￥14,906: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchelsea vacation rentals

1. White Haven - with 2 double rooms

Winchelsea Beach

"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...

Emma V.

￥46,445 total

includes taxes & fees

Sep 6 - Sep 7

2. Sparrows Den Lodge

Winchelsea

￥86,351 total

includes taxes & fees

Sep 8 - Sep 9

3. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

￥63,968 total

includes taxes & fees

Sep 25 - Sep 26

4. Extraordinary Huts

Rye

Diana

￥31,179 total

includes taxes & fees

Sep 21 - Sep 22

5. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

East Sussex

Mark

￥30,232 total

includes taxes & fees

Sep 10 - Sep 11

6. 3 Cinque Ports Street

Rye

￥90,227 total

includes taxes & fees

Sep 16 - Sep 17

7. Rhodown - sun on the terrace all round

Hastings

William E.

￥48,979 total

includes taxes & fees

Sep 5 - Sep 6

8. An unusual two-storey apartment with beams and an open fire.

Rye

Robert E.

￥49,190 total

includes taxes & fees

Sep 6 - Sep 7

9. 2 bedroom accommodation in Rye

Rye

Sheila Davies

￥49,190 total

includes taxes & fees

Sep 27 - Sep 28

10. Caravan With Decking&patio-8/10 Berth-pet Friendly

Rye

Kerry

￥36,481 total

includes taxes & fees

Oct 5 - Oct 6

11. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

￥15,842 total

includes taxes & fees

Sep 6 - Sep 7

12. Charming 3-bedroom house in soothing Playden Rye neighborhood

Playden, Rye

Edward W.

￥69,669 total

includes taxes & fees

Sep 8 - Sep 9

13. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

Hastings

"We had a very pleasant stay at this spacious and comfortable home, which was well-suited for our larger group. The garden was a particular highlight, offering ample space and the added delight of fresh fruit to pick. The location is great, being within a short walking distance of the beach and sea (20mins). The property was generally tidy, there were a few spiderwebs which luckily didn't have any spiders. If these were removed it would enhance the experience. Parking proved somewhat challenging...

Tabassum A.

￥75,960 total

includes taxes & fees

Sep 7 - Sep 8

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

Rye

Anonymous traveler

￥42,910 total

includes taxes & fees

Sep 30 - Oct 1

15. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

Camber Rye

"Such a beautiful caravan. We went at Easter 2026 and there were beautiful Easter touches bunnies etc throughout the caravan. Chocolates and Proscecco were a lovely touch. Checking in process was seamless and they provided so much helpful information. Would recommend and will definitely be back for another stay. Dog friendly too, my dogs loved the warm cozy throws provided and enclosed gated decking area"

Claire O.

￥41,390 total

includes taxes & fees

Sep 5 - Sep 6

16. 1A Coastguard Cottages

Rye

￥105,947 total

includes taxes & fees

Sep 19 - Sep 20

17. 4 bedroom accommodation in Pett

Pett

Sarah Gunner

￥107,036 total

includes taxes & fees

Sep 10 - Sep 11

18. Bexlet

Bexhill-on-Sea

Tim

￥17,734 total

includes taxes & fees

Sep 28 - Sep 29

19. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Camber

￥45,770 total

includes taxes & fees

Oct 1 - Oct 2

20. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

￥34,742 total

includes taxes & fees

Sep 28 - Sep 29

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winchelsea Hotel Reviews

The View Hotel

10/10 Excellent

"Lovely staff clean and tidy. Well managed. Comfortable"

Majestic Hotel Eastbourne by Belvilla

8/10 Good

"It looked like it was decorated in the 1990s and probably looked fantastic back then. It was dated and shabby. There was a feel of a horror film when we arrived. However, the breakfast was tasty. Staff were really helpful although for such a large place they had few staff. It was a bit lifeless with the bar not being open, we had to have a hot drink in our room. Unfortunately, the rooms were like saunas even with opening windows. Everything was clean but a bit run down. I think the price was reasonable for the experience and location. I would book again. Cheap and cheerful."

Cavendish Hotel

8/10 Good

"It's a grand old building - and some of the public areas downstairs are nicely done, and look great. Big and spacious reception/foyer and bar area as well (Didn't use the restaurant). The room was a good size, and a decent price - but as wih many of these big, old properties, it's worn & tired. It was cleaned well, and plenty of space."

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
Use the map to find apartments and other holiday homes in the Winchelsea neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Winchelsea while they last

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

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?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This vacation home rental near Winchelsea offers an indoor pool, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Winchelsea?

With 14 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 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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchelsea vacation rentals

1. White Haven - with 2 double rooms

2. Sparrows Den Lodge

3. 1 bedroom accommodation in Winchelsea Beach, near Rye

4. Extraordinary Huts

5. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

6. 3 Cinque Ports Street

7. Rhodown - sun on the terrace all round

8. An unusual two-storey apartment with beams and an open fire.

9. 2 bedroom accommodation in Rye

10. Caravan With Decking&patio-8/10 Berth-pet Friendly

11. Chestnut Meadow Camping

12. Charming 3-bedroom house in soothing Playden Rye neighborhood

13. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

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

15. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

16. 1A Coastguard Cottages

17. 4 bedroom accommodation in Pett

18. Bexlet

19. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

20. Cabin - Sleeps 8 - Garden and Parking

Find vacation rentals that suit your style

Top Winchelsea Hotel Reviews

The View Hotel

The Cumberland Hotel

The George in Rye

Majestic Hotel Eastbourne by Belvilla

Ashford International Hotel & Spa

The Lookout Rye

Cavendish Hotel

OYO Stade Court Hotel

The Grand Hotel Eastbourne

Find out more about Winchelsea

Frequently asked questions

Go further with the Expedia app