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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Winchelsea vacation homes

Cottage | Interior
Sparrows Den Lodge

Vacation Home in Winchelsea

Sparrows Den Lodge
3.5 star property
The price is AED 1,537
AED 1,845 total
includes taxes & fees
27 Dec - 28 Dec
Sparrows Den Lodge
Marina
Peaceful Retreat, Sovereign Harbour, Eastbourne - FREE WELCOME PACK

Vacation Home in Eastbourne

Peaceful Retreat, Sovereign Harbour, Eastbourne - FREE WELCOME PACK
10.0 out of 10, Exceptional, (50)
"Nice welcome package and good proactive communication.We will definitely come back."
Germany
Joerg T.
The price is AED 673
AED 934 total
includes taxes & fees
11 Jan - 12 January 2026
Peaceful Retreat, Sovereign Harbour, Eastbourne - FREE WELCOME PACK
Interior
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters

Vacation Home in Hastings

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
"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...
United Kingdom
Tabassum A.
The price is AED 260
AED 1,513 total
includes taxes & fees
4 Jan - 5 January 2026
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
TV
Camber Sands Holiday Park

Vacation Home in Sussex

Camber Sands Holiday Park
2.0 star property
The price is AED 377
AED 598 total
includes taxes & fees
3 Jan - 4 January 2026
Camber Sands Holiday Park
Interior
"The Gateway to Birling Gap + Seven Sisters- RB&B Living

Vacation Home in Eastbourne City Centre

"The Gateway to Birling Gap + Seven Sisters- RB&B Living
2.0 star property
The price is AED 334
AED 334 total
includes taxes & fees
18 Jan - 19 January 2026
"The Gateway to Birling Gap + Seven Sisters- RB&B Living
Interior
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Vacation Home in Tenterden

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
9.6 out of 10, Exceptional, (13)
"Fantastic can’t fault anything will definitely be back 5star accommodation "
United Kingdom
Shaun M.
The price is AED 1,002
AED 1,002 total
includes taxes & fees
6 Jan - 7 January 2026
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Property grounds
Calm Private Apartment – Ideal to Work, Rest & Explore

Vacation Home in Ashford

Calm Private Apartment – Ideal to Work, Rest & Explore
2.0 star property
The price is AED 540
AED 540 total
includes taxes & fees
23 Dec - 24 Dec
Calm Private Apartment – Ideal to Work, Rest & Explore
Beach nearby
Lovely 2 Bedroom Flat in a heart of Eastbourne, East Sussex

Vacation Home in Eastbourne City Centre

Lovely 2 Bedroom Flat in a heart of Eastbourne, East Sussex
9.8 out of 10, Exceptional, (8)
"Nice & clean comfortable apartment.Close to everything needed ."
United Kingdom
Darren E.
The price is AED 983
AED 1,204 total
includes taxes & fees
2 Jan - 3 January 2026
Lovely 2 Bedroom Flat in a heart of Eastbourne, East Sussex
Exterior
Step back in time - stay in the beautiful medieval house in the center of Rye

Vacation Home in Rye

Step back in time - stay in the beautiful medieval house in the center of Rye
2.0 star property
The price is AED 752
AED 1,130 total
includes taxes & fees
23 Dec - 24 Dec
Step back in time - stay in the beautiful medieval house in the center of Rye
Property grounds
New beach holiday park spacious family caravan

Vacation Home in Dymchurch

New beach holiday park spacious family caravan
6.0 out of 10, (1)
The price is AED 614
AED 698 total
includes taxes & fees
22 Dec - 23 Dec
New beach holiday park spacious family caravan
Terrace/patio
East Sussex Manor | Sleeps 12 | Hot Tub & Parking

Vacation Home in East Sussex

East Sussex Manor | Sleeps 12 | Hot Tub & Parking
8.0 out of 10, Very Good, (1)
"Nice property. Lovely having hot tub and big table in conservatory to eat together and play games in the evening. Comfortable rooms (more bedside tables would be good addition). Kitchen good - lots plates, bowls, cutlery but could be better equipped - No larger pans, or oven cookware, no larger serving bowls (so we served salad from a frying pan), no glass containers for microwave cooking. Blocked shower upstairs - managed to unblock. No toilet roll - would have been appreciated after...
United Kingdom
Lindsey C.
The price is AED 1,191
AED 1,780 total
includes taxes & fees
15 Jan - 16 January 2026
East Sussex Manor | Sleeps 12 | Hot Tub & Parking
Property grounds
The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel

Vacation Home in Hythe

The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel
7.4 out of 10, Good, (3)
"Nice little house, not too far from the huddle and bustle, on a very lovely steep hill( hence the view)"
Netherlands
Edith S.
The price is AED 639
AED 727 total
includes taxes & fees
22 Dec - 23 Dec
The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel
Fridge, microwave, oven, stovetop
Family-friendly countryside home with hot tub, swing set and trampoline

Vacation Home in Battle

Family-friendly countryside home with hot tub, swing set and trampoline
2.0 star property
The price is AED 1,026
AED 1,222 total
includes taxes & fees
22 Dec - 23 Dec
Family-friendly countryside home with hot tub, swing set and trampoline
Smart TV, DVD player, books
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Vacation Home in Hellingly /Hailsham

Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
7.6 out of 10, Good, (9)
"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 AED 1,450
AED 2,639 total
includes taxes & fees
4 Jan - 5 January 2026
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
TV
suspire House -Sleeps6-Garden-Bbq-Coastal retreat

Vacation Home in New Romney

suspire House -Sleeps6-Garden-Bbq-Coastal retreat
The price is AED 835
AED 1,032 total
includes taxes & fees
4 Jan - 5 January 2026
suspire House -Sleeps6-Garden-Bbq-Coastal retreat
Smart TV, fireplace, books, stereo
Writers Retreat in the heart of Ashford Town

Vacation Home in Ashford

Writers Retreat in the heart of Ashford Town
The price is AED 757
AED 1,057 total
includes taxes & fees
22 Dec - 23 Dec
Writers Retreat in the heart of Ashford Town
Exterior
Chequer - a holiday let that sleeps 14 guests in 7 bedrooms

Vacation Home in Rye

Chequer - a holiday let that sleeps 14 guests in 7 bedrooms
10.0 out of 10, Exceptional, (1)
"We had such a lovely time staying at Chequer. The location was perfect, and the house itself was beautiful, spacious, and so comfortable. Every detail felt thoughtfully considered, which made it a real home away from home. We’d be very happy to stay again and highly recommend it."
United States
Anonymous traveler
The price is AED 14,036
AED 14,036 total
includes taxes & fees
6 Jan - 7 January 2026
Chequer - a holiday let that sleeps 14 guests in 7 bedrooms
Cottage | Living room
3 Tidal

Vacation Home in Rye

3 Tidal
3.5 star property
The price is AED 1,583
AED 1,900 total
includes taxes & fees
27 Dec - 28 Dec
3 Tidal
Interior
Charming 8-Bedroom Retreat in Rural Kent Village

Vacation Home in Sellindge

Charming 8-Bedroom Retreat in Rural Kent Village
The price is AED 4,664
AED 5,863 total
includes taxes & fees
22 Dec - 23 Dec
Charming 8-Bedroom Retreat in Rural Kent Village
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

The Chatsworth Hotel

The Chatsworth Hotel

10/10 Excellent
"Excellent room exceptional staff very friendly and clean good food and very reasonable prices across the board, bar prices very fair. We can high recommend this hotel Adrian & Annabelle Straatman Wyberton Boston Lincolnshire UK"
Adrian 3-night trip
Posted 19 hours ago
The Chatsworth Hotel