Holiday Rentals in Winchelsea

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Our top choices for Winchelsea holiday rentals

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 €266
includes taxes & fees
7 Mar - 8 Mar
Grogu's Rest - 2 bedrooms with decking sleeps 6

1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (11 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
The price is €405
includes taxes & fees
13 Feb - 14 Feb
1 bedroom accommodation in Winchelsea Beach, near Rye

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is €434
includes taxes & fees
1 Mar - 2 Mar
Sparrows Den Lodge

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 €253
includes taxes & fees
1 Mar - 2 Mar
White Haven - with 2 double rooms

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
The price is €96
includes taxes & fees
8 Feb - 9 Feb
Chestnut Meadow Camping

Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (31 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is €186
includes taxes & fees
9 Feb - 10 Feb
Pinewood Camping Pods - At Port Lympne Reserve

Beach Lodge - 5 minute walk to the sandy beach

Beach Lodge - 5 minute walk to the sandy beach
Camber
8.8 out of 10, Excellent, (10 reviews)
"Fantastic lodge near the beach on a great location in the park. Highly recommend "
United Kingdom
Laura J.
The price is €266
includes taxes & fees
8 Feb - 9 Feb
Beach Lodge - 5 minute walk to the sandy beach

Calm Private Annex Ideal to Work, Rest & Explore

Calm Private Annex Ideal to Work, Rest & Explore
2.0 star property
Ashford
10.0 out of 10, Exceptional, (1 review)
"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 €97
includes taxes & fees
4 Mar - 5 Mar
Calm Private Annex Ideal to Work, Rest & Explore

White Hart Netherfield

White Hart Netherfield
2.0 star property
Battle
The price is €103
includes taxes & fees
11 Feb - 12 Feb
White Hart Netherfield

Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
9.0 out of 10, Wonderful, (96 reviews)
"Great stay"
United Kingdom
George
Osborne Apartments

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (11 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
The price is €137
includes taxes & fees
11 Feb - 12 Feb
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Gun Hill Cottage

Gun Hill Cottage
3.5 star property
Heathfield
10.0 out of 10, Exceptional, (2 reviews)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
United Kingdom
Thomas
The price is €827
includes taxes & fees
10 Feb - 11 Feb
Gun Hill Cottage

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (50 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is €91
includes taxes & fees
10 Feb - 11 Feb
Bexlet

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
Mersham
10.0 out of 10, Exceptional, (3 reviews)
"WE had an excellent stay with our two young grandchildren. It was perfectly located as we had visited Chatham historic dockyard and spending the next day at Tenterden heritage railway. So much so the youngest wanted to stay an extra night! The description is spot on, Our host extremely helpful with local knowledge. Highly recommend "
United Kingdom
Malcolm T.
The price is €177
includes taxes & fees
9 Feb - 10 Feb
2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.

Victory - idyllic holiday home in Hastings

Victory - idyllic holiday home in Hastings
Hastings
10.0 out of 10, Exceptional, (1 review)
"Nice and Memorable stay "
United Kingdom
Kishore S.
The price is €253
includes taxes & fees
15 Feb - 16 Feb
Victory - idyllic holiday home in Hastings

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 €175
includes taxes & fees
1 Mar - 2 Mar
Extraordinary Huts

House - Sleeps 6 & Parking

House - Sleeps 6 & Parking
2.0 star property
Ashford
The price is €227
includes taxes & fees
22 Feb - 23 Feb
House - Sleeps 6 & Parking

Family Caravan Rental 2 bed Caravan

Family Caravan Rental 2 bed Caravan
2.0 star property
Hastings
The price is €139
includes taxes & fees
8 Feb - 9 Feb
Family Caravan Rental 2 bed Caravan

Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.2 out of 10, Wonderful, (5 reviews)
"Lovely peaceful setting and the caravan had everything you would need and bonus being so close to Hastings"
United Kingdom
William E.
The price is €266
includes taxes & fees
1 Mar - 2 Mar
Rhodown - sun on the terrace all round

Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
Hythe
9.0 out of 10, Wonderful, (2 reviews)
"Property clean & adequate...owner very pleasant & helpful."
United Kingdom
Jayne
The price is €85
includes taxes & fees
3 Mar - 4 Mar
Pet Friendly Private Cabin Town Eurotunnel Beach
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, 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 €151 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?

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winchelsea?

With 6 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.