Winchelsea Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Winchelsea holiday rentals

Flat-screen TV

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 HK$882
HK$2,435 total
includes taxes & fees
17 Mar - 18 Mar
Grogu's Rest - 2 bedrooms with decking sleeps 6
Interior

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is HK$3,339
HK$4,007 total
includes taxes & fees
15 Mar - 16 Mar
Sparrows Den Lodge
Exterior

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 HK$756
HK$2,309 total
includes taxes & fees
12 Mar - 13 Mar
White Haven - with 2 double rooms
Room

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
The price is HK$729
HK$875 total
includes taxes & fees
12 Mar - 13 Mar
Chestnut Meadow Camping
Flat-screen TV

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 HK$1,133
HK$2,687 total
includes taxes & fees
12 Mar - 13 Mar
River View - Overlooking the river
TV

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 HK$882
HK$2,435 total
includes taxes & fees
12 Mar - 13 Mar
Rhodown - sun on the terrace all round
Outdoor dining

White Hart Netherfield

White Hart Netherfield
2.0 star property
Battle
The price is HK$787
HK$945 total
includes taxes & fees
30 Mar - 31 Mar
White Hart Netherfield
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$945
HK$1,217 total
includes taxes & fees
1 Apr - 2 Apr
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
Exterior

The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
The price is HK$1,216
HK$1,584 total
includes taxes & fees
17 Mar - 18 Mar
The Field View 2 by Tiny Away
Garden

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 HK$787
HK$945 total
includes taxes & fees
17 Mar - 18 Mar
Calm Private Annex in Ashford Ideal to Work, Rest & Explore
Bar (on property)

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Tenterden
The price is HK$2,322
HK$2,322 total
includes taxes & fees
15 Mar - 16 Mar
Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Miscellaneous

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 HK$691
HK$829 total
includes taxes & fees
18 Mar - 19 Mar
Bexlet
Free WiFi

1066 Apart Hotel

1066 Apart Hotel
2.0 star property
Hastings
8.0 out of 10, Very good, (1 review)
The price is HK$531
HK$743 total
includes taxes & fees
25 Mar - 26 Mar
1066 Apart Hotel
1 bedroom, free WiFi, bed sheets

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 HK$1,154
HK$1,322 total
includes taxes & fees
14 Mar - 15 Mar
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Exterior

Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite

Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite
Flimwell, Wadhurst
9.4 out of 10, Exceptional, (3 reviews)
"Our trip to the Shepherds Hut was nothing short of idyllic! Our host Jay was so helpful and kind, even going so far as to give us a lift to Tunbridge Wells when our pre-booked taxi didn't show up. The outdoor kitchen was so easy to use, and made an al fresco breakfast very lovely. We took full advantage of the firepit - logs and kindling provided for us - as well as the lovely walks nearby. I would recommend to anyone looking to get away for a bit of peace and beauty!"
United Kingdom
Josi K.
The price is HK$756
HK$924 total
includes taxes & fees
15 Mar - 16 Mar
Luxury Shepherds Hut, w/large garden, firepit, & Wi-Fi @ Cedar Gables Campsite
Interior

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.6 out of 10, Exceptional, (14 reviews)
"We had a great stay at Goldings. The accommodation was lovely and the hot tub was great. The staff were all really friendly and helpful. The food and drink on site was great too."
United States
Anonymous traveller
The price is HK$2,322
HK$2,322 total
includes taxes & fees
12 Mar - 13 Mar
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Property grounds

The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom

The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom
Ashford
9.8 out of 10, Exceptional, (27 reviews)
"Thank you - we had a fantastic time and will definitely return! Host was responsive and very helpful, the local recommendations were perfect and we had the relaxing time we were after."
United States
Anonymous traveller
The price is HK$2,022
HK$2,022 total
includes taxes & fees
17 Mar - 18 Mar
The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom
Fishing

1 bedroom accommodation in Pevensey Bay, near Eastbourne

1 bedroom accommodation in Pevensey Bay, near Eastbourne
Pevensey Bay, near Eastbourne
10.0 out of 10, Exceptional, (13 reviews)
"We. Had a lovely holiday right near the beach had some lovely walks. The accommodation was very nice and clean. The owner was excellent and very accommodating if we needed anything."
United States
Christine Sheen
The price is HK$1,774
HK$1,774 total
includes taxes & fees
19 Mar - 20 Mar
1 bedroom accommodation in Pevensey Bay, near Eastbourne
Living room

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 HK$1,550
HK$1,550 total
includes taxes & fees
12 Mar - 13 Mar
Extraordinary Huts
1 bedroom, iron/ironing board, WiFi, bed sheets

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 HK$777
HK$777 total
includes taxes & fees
30 Mar - 31 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

Marine Parade Hotel

Marine Parade Hotel

6/10 Okay
"Shops and beach nearby "
Christopher 4-night trip
Posted 2 days ago
Marine Parade Hotel

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:

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

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.