Winchelsea Holiday Rentals

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Our top choices for Winchelsea holiday rentals

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is NZ$850
includes taxes & fees
6 Mar - 7 Mar
Sparrows Den Lodge

Grogu's Rest - 2 bedrooms with decking sleeps 6

Grogu's Rest - 2 bedrooms with decking sleeps 6
Winchelsea Beach
8.8 out of 10, Excellent, (8 reviews)
"great stay again"
United Kingdom
lindsay r.
The price is NZ$522
includes taxes & fees
15 Mar - 16 Mar
Grogu's Rest - 2 bedrooms with decking sleeps 6

White Haven - with 2 double rooms

White Haven - with 2 double rooms
Winchelsea Beach
2.0 out of 10, (1 review)
"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 NZ$495
includes taxes & fees
16 Mar - 17 Mar
White Haven - with 2 double rooms

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
The price is NZ$187
includes taxes & fees
8 Mar - 9 Mar
Chestnut Meadow Camping

Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.4 out of 10, Exceptional, (32 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is NZ$322
includes taxes & fees
4 Mar - 5 Mar
Pinewood Camping Pods - At Port Lympne Reserve

River View - Overlooking the river

River View - Overlooking the river
Rye Harbour
8.8 out of 10, Excellent, (21 reviews)
"Fantastic stay amazing location and very luxurious"
United Kingdom
nicholas t.
The price is NZ$575
includes taxes & fees
15 Mar - 16 Mar
River View - Overlooking the river

White Hart Netherfield

White Hart Netherfield
2.0 star property
Battle
The price is NZ$205
includes taxes & fees
15 Mar - 16 Mar
White Hart Netherfield

1066 Apart Hotel

1066 Apart Hotel
2.0 star property
Hastings
The price is NZ$167
includes taxes & fees
18 Mar - 19 Mar
1066 Apart Hotel

The Boathouse

The Boathouse
3.0 star property
St Leonards-On-Sea
10.0 out of 10, Exceptional, (1 review)
The price is NZ$937
includes taxes & fees
12 Mar - 13 Mar
The Boathouse

Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (41 reviews)
"Escaping to the country has never been more fun and magical. The resident robin and all his many friends keep you in that chilled mindset. The town of Rye was 10 mins by car and full of historical charm. It was even being used for filming while we visited. We walked from Rye to Camber sands along the cycle path and there are frequent buses back. "
United Kingdom
Meryl
The price is NZ$332
includes taxes & fees
8 Mar - 9 Mar
Extraordinary Huts

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.8 out of 10, Excellent, (51 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is NZ$178
includes taxes & fees
12 Mar - 13 Mar
Bexlet

Calm Private Annex in Ashford Ideal to Work, Rest & Explore

Calm Private Annex in Ashford Ideal to Work, Rest & Explore
2.0 star property
Ashford
7.4 out of 10, Good, (3 reviews)
"One night stay to visit local family. Very welcoming, met on arrival. Coldest night of the year so far and it was warm, cosy & comfortable. Owners live next door, attached house, easy parking, easy to find. Will possibly be return during 2026, central location for all our needs."
United Kingdom
Steve
The price is NZ$211
includes taxes & fees
8 Mar - 9 Mar
Calm Private Annex in Ashford Ideal to Work, Rest & Explore

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Bexhill
10.0 out of 10, Exceptional, (6 reviews)
"Fantastic location, perfect flat!"
United Kingdom
Mark S.
The price is NZ$283
includes taxes & fees
4 Mar - 5 Mar
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms

Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
Benenden
9.6 out of 10, Exceptional, (15 reviews)
"A wonderful place for a holiday Nice location. Good opportunity for excursions to Hastings, Tenterden, Bodiam. Stop off at The Bull or the Milkhouse in Sissinghurst."
United States
Hartmut K.
The price is NZ$1,642
includes taxes & fees
8 Mar - 9 Mar
Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms

The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
The price is NZ$342
includes taxes & fees
4 Mar - 5 Mar
The Field View 2 by Tiny Away

Lakeside Lodge - Warrenwood Country Park

Lakeside Lodge - Warrenwood Country Park
East Sussex
10.0 out of 10, Exceptional, (1 review)
"The property was so much nicer than the pictures suggested. My friends and I enjoyed a simple and scenic Christmas. The booking was easy and the staff were understanding. Would definitely come back again."
United Kingdom
Firdest K.
The price is NZ$672
includes taxes & fees
13 Mar - 14 Mar
Lakeside Lodge - Warrenwood Country Park

Henley Bridge Holiday Cottage

Henley Bridge Holiday Cottage
Ashburnham, near Battle
8.4 out of 10, Very good, (5 reviews)
"A very peaceful area and cosy cottage with all we could need."
United Kingdom
Lynda M.
The price is NZ$663
includes taxes & fees
12 Mar - 13 Mar
Henley Bridge Holiday Cottage

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
10.0 out of 10, Exceptional, (1 review)
"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 NZ$471
includes taxes & fees
4 Mar - 5 Mar
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Lilyrose Cottage

Lilyrose Cottage
3.0 star property
Pevensey
10.0 out of 10, Exceptional, (1 review)
"All very good. However too many disabled parking spaces meaning too few for others"
United Kingdom
Graeme
The price is NZ$976
includes taxes & fees
12 Mar - 13 Mar
Lilyrose Cottage

Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
Hellingly /Hailsham
7.6 out of 10, Good, (9 reviews)
"The property was incredible and the host had incredible communication. Maria could not have been more accommodating and we cannot thank her enough, we had a fabulous stay and hope to be back soon."
United Kingdom
Matilda B.
The price is NZ$1,327
includes taxes & fees
10 Mar - 11 Mar
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
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, 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$205 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?

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly: 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 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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 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.