Photo by John Scale

Search Cottages in Winchelsea

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 390 Cottages in Winchelsea with updated reviews, rates, and availability.

Converted stable in secluded rural setting.
Exterior

Converted stable in secluded rural setting.

10.0 out of 10, Exceptional, (135)
"The property is probably the cleanest we’ve stayed in. Picture sitting looking out the window watching the birds on the feeders Wood burner crackling drink in hand music on perfect. Lovely property with all you could need "
Converted stable in secluded rural setting.
Coastguard Cottage With Sea Views
Outdoor dining

Coastguard Cottage With Sea Views

9.8 out of 10, Exceptional, (65)
"We found the cottage to be very comfortable and well equipped. Great walks direct from the front door especially to The Cove for a very enjoyable early dinner. We all agreed it is one of the nicest places we have stayed in. We would love to return in the summer to really explore the area and see the views on sunny days."
Coastguard Cottage With Sea Views
The Parlour - Spectacular views, country walks, cozy nights, pet friendly.
Terrace/patio

The Parlour - Spectacular views, country walks, cozy nights, pet friendly.

10.0 out of 10, Exceptional, (120)
"The Parlour is extremely well equipped, spacious and comfortable and Louise the perfect host.I would recommended the property to anyone."
The Parlour - Spectacular views, country walks, cozy nights, pet friendly.
An unusual two storey apartment with beams and open fire.
Exterior

An unusual two storey apartment with beams and open fire.

10.0 out of 10, Exceptional, (8)
"We stayed here for a weekend, to attend a wedding nearby - two adults and two children (aged 5 & 9). The configuration of the apartment was perfect: there are two double beds on the top floor, all kind of in the same room but separated by a wall (it makes sense once you see it), which was perfect for us. Really, really cute place oozing with character, and a very friendly vibe (again, that makes sense once you see it). Well provisioned kitchen (our catering needs didn't extend beyond making...
The price is AED 612
AED 612 total
includes taxes & fees
6 Mar - 7 Mar
An unusual two storey apartment with beams and open fire.
Cosy Seaside Cottage sleeps 6 pets welcome
Exterior

Cosy Seaside Cottage sleeps 6 pets welcome

10.0 out of 10, Exceptional, (4)
"Very happy with the house and location. Tasteful decoration. Good size rooms. Lovely garden. Parking for 2 cars. Responsive, helpful hosts."
Cosy Seaside Cottage sleeps 6 pets welcome
2 bedroom accommodation in Lydd, Romney Marsh
Living area

2 bedroom accommodation in Lydd, Romney Marsh

2 bedroom accommodation in Lydd, Romney Marsh
2 bedroom accommodation in Hailsham
Exterior

2 bedroom accommodation in Hailsham

10.0 out of 10, Exceptional, (4)
"A picture perfect cottage that is well appointed and very dog friendly. The cottage was in easy reach many of the towns on the coast, however we stayed because of its close location for a wedding and reception. "
2 bedroom accommodation in Hailsham
3 bedroom accommodation in Near Tenterden
Exterior

3 bedroom accommodation in Near Tenterden

9.8 out of 10, Exceptional, (7)
"Excellent all round Beautiful house great hosts and we were able to use the pool Would love to return"
3 bedroom accommodation in Near Tenterden
4 Star Luxury Romantic Break - The Pavilion at Brunger House (Dog Friendly)
Exterior

4 Star Luxury Romantic Break - The Pavilion at Brunger House (Dog Friendly)

9.8 out of 10, Exceptional, (9)
"We enjoyed our stay at the pavilion. It was spotless & a great welcome pack was provided. We were warmly greeted. The pavilion is in a peaceful location & within walking distance of Tenterden. Also nearby to local wineries."
4 Star Luxury Romantic Break - The Pavilion at Brunger House (Dog Friendly)
Wheelwrights Cottage - beautiful cottage by Bloom Stays, sleeping 5 guests in 3 bedrooms
Living area

Wheelwrights Cottage - beautiful cottage by Bloom Stays, sleeping 5 guests in 3 bedrooms

9.6 out of 10, Exceptional, (11)
"We stayed for four nights in June and were delighted with the facilities provided. One king size bedroom, one double bedroom and a small room suitable for a child (we brought our own crib for the baby). Small details like the stair gate and a few toys helped too. The patio furniture was well used as we had glorious weather. Staplecross is well placed for exploring Rye. Hastings, local vineyards and National Trust properties. We would like to return next year!"
Wheelwrights Cottage - beautiful cottage by Bloom Stays, sleeping 5 guests in 3 bedrooms
Eeyores House - UK43487
Exterior

Eeyores House - UK43487

10.0 out of 10, Exceptional, (1)
"Firstly I need to say how wonderful Jim and Anita were and how welcoming they made us all feel. The location of Honey Pot Farm is stunning with views to take your breath away. The town of Hythe is a mere 10min drive and well worth a visit. We will most defiantly be going back 10/10"
Eeyores House - UK43487
1 bedroom accommodation in St Leonards-on-Sea, near Hastings
Interior

1 bedroom accommodation in St Leonards-on-Sea, near Hastings

10.0 out of 10, Exceptional, (15)
1 bedroom accommodation in St Leonards-on-Sea, near Hastings
2 bedroom accommodation in Herstmonceux, near Hailsham
Living area

2 bedroom accommodation in Herstmonceux, near Hailsham

10.0 out of 10, Exceptional, (26)
"Absolutely wonderful stay. Fantastic hosts - exceptionally professional and kind. Can't say enough good things about the experience."
2 bedroom accommodation in Herstmonceux, near Hailsham
2 bedroom accommodation in Goudhurst
Living area

2 bedroom accommodation in Goudhurst

10.0 out of 10, Exceptional, (13)
"A cosy cottage with a ‘home from home’ ambience. Caroline & Mark have thought of everything; a well equipped kitchen, lots of reading material relating to the locale, maps, walks and games. We wished we had booked for a longer stay, but intend to return in order to visit the many places of interest that are close by."
2 bedroom accommodation in Goudhurst
2 bedroom accommodation in Wadhurst, near Tunbridge Wells
Property grounds

2 bedroom accommodation in Wadhurst, near Tunbridge Wells

10.0 out of 10, Exceptional, (11)
"We had a great stay in this lovely little property on a working farm. The farmers were very friendly and obliging. There are so many gardens and houses to visit in the area and we got to the coast as well. We hope to return one day."
2 bedroom accommodation in Wadhurst, near Tunbridge Wells
Camber Sands Lodge
Exterior

Camber Sands Lodge

3.0 star property
8.0 out of 10, Very Good, (1)
"very close to the beach, just over the road, its better less stony if you walk about 10 mins to the right, about 5 min walk to reception, lodge is located in a quiet park of the park, I always take a tv as my son is socially anxious, and didnt leave the lodge at all, until we left, I felt it would of been useful to have a tv in the double room, as my son took over the only tv, with his xbox, and i got sent to my room, to watch tv, it was nice having the decking outside, could do with outdoor...
Camber Sands Lodge
2 bedroom accommodation in Burwash
Exterior

2 bedroom accommodation in Burwash

10.0 out of 10, Exceptional, (24)
2 bedroom accommodation in Burwash
You’ll find Garden Cottage down a quiet country lane.
Room

You’ll find Garden Cottage down a quiet country lane.

9.6 out of 10, Exceptional, (8)
You’ll find Garden Cottage down a quiet country lane.
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Exterior

16th Century Cottage Situated Opposite The Medieval Landgate Arch

9.6 out of 10, Exceptional, (174)
"The property lies right in the heart of a very cute town. Enjoyed our stay"
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Beach Front Cottage with Direct Access to Stunning Sandy Beach, Dunes & Sea View
Breakfast at low tide

Beach Front Cottage with Direct Access to Stunning Sandy Beach, Dunes & Sea View

10.0 out of 10, Exceptional, (51)
"The sunrooms were amazing fantastic view of the beautiful beach. Property was well kitted out, very comfortable and a really good location. It was a good property for my 89 year old mother as she was able to sleep downstairs. The Owl was excellent."
Beach Front Cottage with Direct Access to Stunning Sandy Beach, Dunes & Sea View
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.
Don't see what you're looking for?
See all available properties in Winchelsea
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchelsea

Vive Hotel
Reception

Vive Hotel

4.0 star property
7.6 out of 10, Good, (74)
"Clean spacious room center of town"
The price is AED 382
AED 458 total
includes taxes & fees
16 Mar - 17 Mar
Vive Hotel
Pinewood Camping Pods - At Port Lympne Reserve
Exterior

Pinewood Camping Pods - At Port Lympne Reserve

2.0 star property
9.6 out of 10, Exceptional, (21)
"The pod was Cody and warm. We loved being so close to the lions and hearing them roar ! My family and I loved the whole adventure ! "
The price is AED 484
AED 580 total
includes taxes & fees
9 Mar - 10 Mar
Pinewood Camping Pods - At Port Lympne Reserve
A fabulous Grade II listed converted 14th Century pub. Child and pet friendly
Outdoor dining

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly

9.6 out of 10, Exceptional, (4)
"We booked Mary's wonderful house for a weekend away in December for a catch up with old friends (12 of us in total). We had an amazing time and really recommend the house. It has lots of character from being an old pub called The Star and the rooms were really comfy with almost all of them having their own ensuite bathroom. The kitchen is well equipped and spacious for cooking even for 12 people and we loved the fireplace and piano in the main living room. We didn't get out much due to storms...
A fabulous Grade II listed converted 14th Century pub. Child and pet friendly
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.

Frequently asked questions

Why book your cottage in Winchelsea with Expedia?
Reserving a cottage in Winchelsea is as easy as working out your travel dates and selecting your ideal place for outdoor recreation and relaxation. From high-end retreats to budget-friendly stays and cottages that include amenities like laundry facilities, Expedia has something for all styles and tastes. As for irresistible deals? We’ve got you covered!
How can I find cheap cottages in Winchelsea?
A good way to compare cheap cottages in Winchelsea is with Expedia’s useful filter tool. Tailor your search results by star rating, amenities and budget to discover unbeatable prices with only a few clicks.