1. Sparrows Den Lodge
- Location: Winchelsea
- Price: £449, includes taxes & fees, 22 Nov - 23 Nov, for Our top choices for Winchelsea holiday homes
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Check prices for these dates, 13 – 14 December 2026
Our top choices for Winchelsea holiday homes
2. 3 Tidal
- Location: Rye
- Price: £436, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winchelsea holiday homes
3. Charming 3-bedroom house in soothing Playden Rye neighborhood
- Location: Playden, Rye
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: £308, includes taxes & fees, 18 Nov - 19 Nov, for Our top choices for Winchelsea holiday homes
- Review: Beautiful house and garden near Rye, by Edward W.
4. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds
- Location: Hastings
- Guest rating: 8/10 (Very good, 5 reviews)
- Price: £303, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
- Review: "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..., by Tabassum A.
5. Victorian 1-Bed Home l Hastings Seafront
- Location: Hastings
- Guest rating: 2/10 (1 review)
- Price: £76, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
- Review: The place where it is is in a dirty back street , no parking. Could only get through the front door to see paint cans, ladders and bags of rubbish, could not connect to owner or locate the key in a lock box , so went somewhere else , cannot up load pictures of the place so make your own mind up on this, by GAYNOR A.
6. Boutique 2 Bed Stables
- Location: Battle
- Price: £240, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winchelsea holiday homes
7. Cozy 1-bedroom bungalow on the outskirts of Ashford perfect for relaxing!
- Location: Ashford
- Price: £126, includes taxes & fees, 14 Nov - 15 Nov, for Our top choices for Winchelsea holiday homes
8. Suspire House -sleeps6-garden-bbq-coastal Retreat
- Location: New Romney
- Guest rating: 2/10 (1 review)
- Price: £212, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
- Review: "We left after just 4 hours because the property was nothing like the listing. The photos give a far better impression than the reality. Before arrival, I had to chase the host for check-in instructions as nothing had been sent. Even after calling, I was only given the key safe code. Later that day, after we’d already left, I received an email stating there was a £100 charge per pet, despite the Hotels.com listing clearly advertising “pets go free.” The property appeared to have had only..., by Werner
9. Spacious Private Annex near Ashford
- Location: Ashford
- Price: £93, includes taxes & fees, 17 Nov - 18 Nov, for Our top choices for Winchelsea holiday homes
10. Stylish Modern 2-Bed House in Central Eastbourne with Free Parking, Near Station
- Location: Eastbourne City Centre
- Price: £176, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
11. Boutique 2 Bed Country Barn
- Location: Battle
- Price: £246, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winchelsea holiday homes
12. Eastbourne, Sovereign Harbour, Holiday & Business Stay - FREE WELCOME PACK
- Location: Eastbourne
- Guest rating: 10/10 (Exceptional, 52 reviews)
- Price: £199, includes taxes & fees, 22 Nov - 23 Nov, for Our top choices for Winchelsea holiday homes
- Review: Return visit as peaceful and comfortable as before, by Dave S.
13. Herstmonceux 1905 newly renovated cottage
- Location: Herstmonceux
- Price: £162, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winchelsea holiday homes
14. suspire House -Sleeps6-Garden-Bbq-Coastal retreat
- Location: New Romney
- Price: £210, includes taxes & fees, 14 Nov - 15 Nov, for Our top choices for Winchelsea holiday homes
15. Lovely 2 Bedroom Flat in a heart of Eastbourne, East Sussex
- Location: Eastbourne City Centre
- Guest rating: 9.6/10 (Exceptional, 13 reviews)
- Price: £219, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
- Review: Lovely place for a family of five or less. Cute and clean. Close to restaurants, train station, and shopping area., by Choua
16. Summerhill by Suspire
- Location: Ashford
- Price: £211, includes taxes & fees, 14 Nov - 15 Nov, for Our top choices for Winchelsea holiday homes
17. Hydrangea House - a managed house that sleeps 10 guests in 4 bedrooms
- Location: Hythe
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: £1,109, includes taxes & fees, 21 Nov - 22 Nov, for Our top choices for Winchelsea holiday homes
- Review: 2 families, 4 adults and 4 kids had a brilliant stay. There was plenty of sleeping space, bathrooms and a brilliant large kitchen table to eat and play games on. The hot tub was a real hit, and the fire pit at the end of the garden was great for toasting marshmallows. Location was excellent for walking to the beach, high street and to Waitrose along the peaceful canal. Would highly recommend!, by Anonymous traveller
18. Summerhill by Suspire
- Location: Ashford
- Price: £213, includes taxes & fees, 19 Nov - 20 Nov, for Our top choices for Winchelsea holiday homes
19. Summerhill Manor Retreat - 7 Bedroom House
- Location: Ashford
- Price: £1,368, includes taxes & fees, 14 Nov - 15 Nov, for Our top choices for Winchelsea holiday homes
20. Summerhill Manor Retreat - 7 Bedroom House
- Location: Ashford
- Price: £1,360, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winchelsea holiday homes
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.
Learn more about Winchelsea
This medieval town's cobblestone streets lead to the ancient Court Hall museum and St Thomas' Church with its panoramic views. Climb Strand Hill for sweeping vistas of Romney Marsh or join locals at The New Inn for traditional English pub fare.
Photo by Adam Kumiszcza
Top reviews in Winchelsea
The New Inn
- Location: Winchelsea
- Review: We stayed for one night at The New Inn. A lovely quiet location and such a warm welcome with an open log fire burning as we arrived and lovely friendly staff. We ate downstairs in the evening and the food was both delicious and great value. The full English breakfast was fabulous - my husband said the best he has had for as long as he could remember so compliments to the chef!! We will definitely stay again when next in the area., by Sandra D, 2 November 2016, rated 10/10 Excellent
The Ship Inn
- Location: Rye
- Review: I was really pleased with the Ship,vand a couple of other reviews didn't do it credit at all, in fact I thought the reviewer must have stayed at a different place . It was a last minute business trip, one night stay and the price and location were really good. I had booked a deluxe double but my meeting was called forward by one day so I had to rebook through here and only a standard was available that night, that having been said the room was fine. Yes, it is a 16th Century Inn so the rooms..., by Mark, 7 February 2019, rated 10/10 Excellent
The Hope Anchor
- Location: Rye
- Review: The bedroom was very clean and comfortable. The wide choices at breakfast were excellent. The only slight setback, in my opinion, was the lack of draught beer In the bar. I can't wait to return to this hotel and magical Rye., by John, 30 September 2026, rated 10/10 Excellent
The George in Rye
- Location: Rye
- Review: Stayed for one night at the George in Rye. Right in the centre of town and convenient for browsing the local shops. Stayed in Room 3 which was absolutely gorgeous. The general décor of the hotel is beautiful and the staff were very pleasant and helpful. Had our evening meal there - quite pricey but enjoyable with good service. Breakfast (included in room price) was equally enjoyable but no sign of any toast! I'm sure if we'd asked it would have been provided though. Only downside was no..., by Sharon, 7 October 2015, rated 10/10 Excellent
The Old Borough Arms
- Location: Rye
- Review: The staff were very welcoming,friendly and served a delicious Vegetarian Breakfast in record time.Rye is a delightful place with lots to see, do,and places to eat and drink.Not to mention the lovely array of independent shops.I would certainly return to the Old Borough arms as I loved the relaxed feel and having your own key to come and go as you please was a real bonus.Far preferable to staying in a hotel,although it had that hotel air about it with a proper iron and board,tea and coffee making..., by Gilly, 19 February 2016, rated 10/10 Excellent
Extraordinary Huts
- Location: Rye
- Review: Away from normal life.beautiful country sides. Lovely views. Property is amazing ,log fire and flume.fully equipped. Kitchen is good .no frifge but cold bix outside .which had pint a milk in it on arrival. No electric plug sockets .unable to dry my hair . Owner leabes a charher to conct your phones. Comfortable cosy ..no tv . Has radio . Close to ruw its self. Very romantic ., by Anonymous traveller, 5 April 2019, rated 10/10 Excellent
River Haven Hotel
- Location: Rye
- Review: The staff were all very friendly and helpful.The location and parking facilities were great.We very much enjoyed our stay and would certainly recommend this hotel to anyone wanting to stay in Rye., by Susan, 6 September 2026, rated 10/10 Excellent
The Lookout Rye
- Location: Rye
- Review: Great hotel and location for centre of Rye and its surrounding attractions via the bus station - 313 bus to Rye Harbour, 10 minutes and Stop B for Camber Sands, 15 minutes. Hotel was lovely and staff friendly and helpful. Room No1 was very spacious for 2. Great tea/coffee facilities, hairdryer and ironing board/iron if you so wished. The room itself needed updating and redecorating and the curtain was torn. The furniture was damaged and dated. The dressing gowns and cushions needed a dry clean..., by Devika, 4 September 2024, rated 10/10 Excellent
Flackley Ash Country House Hotel
- Location: Rye
- Review: ABSOLUTELY BRILLIANT ! I cannot fault this hotel in ANY way - we stayed for 2 nights ( having done a day trip to France via the Euro Tunnel ) and absolutely LOVED it ! ( and would most DEFINITELY come back again ) The indoor swimming pool and whirlpool were AMAZING, as was the breakfast ! - ALL you could possibly want ASWELL I as a cooked English ! What more could you ask for ? If you were to ask me to sum this hotel up in 1 word it would be - PERFECT !, by Anonymous traveller, 29 November 2016, rated 10/10 Excellent
Guestling Hall Hotel
- Location: Hastings
- Review: All good, by Ibrahim, 25 October 2026, rated 10/10 Excellent
The Kings Head Rye
- Location: Rye
- Review: Have stayed many times before, we always have a laugh with the staff and breakfast is excellent. Will continue to go back., by Ann, 14 June 2026, rated 10/10 Excellent
The Woolpack Inn Warehorne
- Location: Ashford
- Review: Probably the most quirky place I have stayed, ( except Frog Manor in Cheshire which I think is now closed ) fab relaxed atmosphere, great English wines, the staff are very helpful 👍, by John, 28 June 2025, rated 10/10 Excellent
The Woolpack Hotel
- Location: Tenterden
- Review: Good location, by Karen, 28 May 2019, rated 10/10 Excellent
Holiday Inn Ashford North A20 by IHG
- Location: Ashford
- Review: Very warm welcome and the comfort was superb. The room was always kept clean. The room was so spacious and in a quite corner which was what I needed after an all day conference. I would recommend this hotel to anyone looking for a country feel hotel., by Petros, 17 October 2016, rated 10/10 Excellent
Moore House
- Location: Old Town Hastings
- Review: We had a great stay at Moore House. The only downside was that the top floor got quite hot, but apart from that everything was excellent. The house was clean, comfortable, and had everything we needed. We’d definitely stay again. Overall, a 5-star experience!, by Birute, 5 August 2026, rated 10/10 Excellent
White Lion Tenterden
- Location: Tenterden
- Review: Charming pub in a very good location in Tenterden high street - excellent if visiting Chapeldown or the Kent and Sussex Railway. Our room was very spacious and the bed was super comfy. Staff were very friendly, breakfast was good. and a secure car park is included with the stay. Would highly recommend, by Sara Jane, 26 September 2026, rated 10/10 Excellent
Little Dane Court
- Location: Tenterden
- Review: Absolutely stunning property for those who like a bit of history. Host was so accommodating to our needs. Beds were exceptionally comfortable and we felt so relaxed making the most of the roll top bath. Breakfast was top drawer (loved the sausages especially). Nothing to fault. We’re already booked in for next year!, by Lisa, 21 December 2025, rated 10/10 Excellent
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