Winchelsea Holiday Rentals from NZ$67: Search Short-Term Rentals

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Our top choices for Winchelsea holiday rentals

A mobile home with a covered porch, a fenced yard, and a paved driveway.

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.

includes taxes & fees

27 Oct - 28 Oct

A brick house with a small patio, a white door, and a wooden fence.

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

includes taxes & fees

6 Nov - 7 Nov

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

3. Sparrows Den Lodge

Winchelsea

includes taxes & fees

2 Nov - 3 Nov

A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

4. Extraordinary Huts

Rye

Diana

includes taxes & fees

27 Oct - 28 Oct

A brick wall with a stone base, a wooden gate, and two planters with soil.

5. 3 Cinque Ports Street

Rye

includes taxes & fees

30 Oct - 31 Oct

A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

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

Rye

Robert E.

includes taxes & fees

12 Nov - 13 Nov

A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

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

East Sussex

Alyson B.

includes taxes & fees

1 Nov - 2 Nov

A greenhouse structure surrounded by yellow flowering plants.

8. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

Rye

"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."

Kerry H.

includes taxes & fees

27 Oct - 28 Oct

A wooden staircase leading to a backyard with a garden, a small shed, and a house with a sloped roof.

9. 2 bedroom accommodation in Rye

Rye

Sheila Davies

includes taxes & fees

8 Nov - 9 Nov

A compact kitchen with a stove, oven, sink, and wooden countertops.

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

Rye

Kerry

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a sofa, a coffee table, and a dining area with a table set for four.

11. 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.

includes taxes & fees

1 Nov - 2 Nov

A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

12. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

includes taxes & fees

27 Oct - 28 Oct

A river with a boat, surrounded by greenery and buildings.

13. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Hastings

Melanie G.

includes taxes & fees

1 Nov - 2 Nov

A modern bedroom with a large bed, a bedside table, a desk, and a window.

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

Rye

Anonymous traveller

includes taxes & fees

27 Oct - 28 Oct

A row of white houses with brown roofs and a sandy beach in the foreground.

15. 16 The Boathouse

Rye

Andrew

includes taxes & fees

4 Nov - 5 Nov

A two-story brick house with a visible front door, a small porch, and a fenced yard.

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

Playden, Rye

Edward W.

includes taxes & fees

27 Oct - 28 Oct

A modern building with a curved facade, multiple balconies, and a grassy area in front.

17. Bexlet

Bexhill-on-Sea

Tim

includes taxes & fees

2 Nov - 3 Nov

A small, single-story building with a porch, a bench, and a pathway leading to the entrance.

18. Pinewood Camping Pods - At Port Lympne Reserve

Hythe

Lesley

includes taxes & fees

2 Nov - 3 Nov

A compact living space with a kitchenette, dining area, and seating area.

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

Camber

includes taxes & fees

2 Nov - 3 Nov

20. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

includes taxes & fees

2 Nov - 3 Nov

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Top Winchelsea Hotel Reviews

Cavendish Hotel

10/10 Excellent

"Good hotel"

Majestic Hotel Eastbourne by Belvilla

10/10 Excellent

"Great service from the reception staff. The rooms were very clean and surprisingly large. It was nice to have the sea view. The only downside for us was the lack of parking nearby. It was very hit and miss on getting a spot near the hotel and with a disabled traveller in our group we needed this. If you don't mind the parking issue then this is a great value for money place to stay."

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$67 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?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This holiday home rental outside of 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 holiday with a garden and 1 hot tub.

How many holiday rentals are there in Winchelsea?

With 14 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.

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Check prices for these dates

Our top choices for Winchelsea holiday rentals

1. White Haven - with 2 double rooms

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

3. Sparrows Den Lodge

4. Extraordinary Huts

5. 3 Cinque Ports Street

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

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

8. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

9. 2 bedroom accommodation in Rye

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

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

12. Chestnut Meadow Camping

13. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

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

15. 16 The Boathouse

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

17. Bexlet

18. Pinewood Camping Pods - At Port Lympne Reserve

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

20. Cabin - Sleeps 8 - Garden and Parking

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

Cavendish Hotel

The Lookout Rye

Hythe Imperial Hotel Spa & Golf

Marine Parade Hotel

The Grand Hotel Eastbourne

Majestic Hotel Eastbourne by Belvilla

The Burlington Hotel

Holiday Inn Ashford Central by IHG

New Wilmington Hotel

Find out more about Winchelsea

Frequently asked questions

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