Item 1 of 31


Winchelsea, East Sussex




4 guests

Bedrooms / beds

2 / 2 King-size beds



Matchbox is a beautiful white weatherboarded, stylish holiday cottage for four in the heart of picturesque Winchelsea, East Sussex.**

On entering the cottage you are met with a modern, calming, contemporary interior. In front of you is the galley style well-equipped kitchen. All the mod cons you would want when staying away from home. A 12 place setting dishwasher, washing machine, microwave and Nespresso coffee machine.

From the kitchen, you have direct access out to a small decked courtyard. A pleasant spot for a morning coffee or an evening BBQ (not currently provided).

The lounge diner is adjacent to the kitchen and is a beautiful spot to enjoy a quiet read, leisurely meals or answer those work emails if you must.

Stairs lead down to the TV snug with a large TV for movie nights in.

Stairs lead up to the first-floor king size bedroom comfortably furnished and with enviable views towards the church. Adjacent to the bedroom is a modern, stylishly finished shower room.

The second flight of stairs lead you to another king-size bedroom, the larger of the two bedrooms with beautiful views of the church. Adjacent to the bedroom is a bathroom with a large bath for lazy holiday soaks and finished to a high standard.

Everything about Matchbox speaks ‘class’ and has been finished to a very high standard. Due to the steep staircases, commonplace with a property of this age, we do not permit children under eight years. We welcome one well-behaved dog and some house rules apply.


guests: 4
Bathrooms: 2
beds: 2 King-size beds
Type: Cottage



Bed linen and hand and bath towels provided
Fully equipped kitchen
Washing machine
Nespresso coffee machine (bring your own capsules)
Hair dryer
Courtyard garden (6' by 10')
Street parking
Dog friendly

Additional Information

One well-behaved dog for an additional £25 fee
Property is located on the High Street so there can be some road noise
Steep & narrow staircases
Courtyard garden is a shared space with the neighbours but designated space for both

House Rules

No smoking
No children under 8 years


May 2024

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18 Reviews

18 Reviews

  • Phillips Family

    Super UK holiday - made even more special when returning to a beautiful village and house, with very comfy beds. Beautiful decor & lovingly looked after house. Everything was thought about. Thank you

  • Anna Harvey

    What a gem! Fab location, stylish decor, beautiful views, great facilities and altogether a perfect place for a staycation. Hosts have paid real attention to the little things like hairdryers and lovely bedlinen. Spotlessly clean, comfortable, parking right outside and even a little village shop. Will be back for sure!

  • Alice H

    Matchbox is a glorious cottage and the perfect long weekend getaway, with beautiful sea views and so close to the gorgeous old town of Rye. Matchbox is so beautifully furnished and has been kept pristine, with a fully equipped kitchen and the softest comfiest beds. It was like staying at a 5 star hotel but with all the cosines of your own home! We had the loveliest time exploring the nearby towns, beaches and countryside and Matchbox was the perfect host. We can’t wait to go back there and can’t recommend it enough!

  • David and Victoria Parmiter

    Matchbox is a lovely, welcoming house; perfect for couples exploring the area. Winchelsea is delightful to wander round and Rye is a short drive away with its restaurants, shops and galleries. Its quirkiness is part of its charm and it is a very grownup house beautifully furnished. A delightful place to stay.

  • Neil & Claire

    We felt very honoured to be the first guests staying at Matchbox. The house was immaculately clean and tastefully decorated with a creative flair. There are many interesting paintings and objects. The kitchen is well equipped and the beds comfortable. Winchelsea is a small, quiet and beautiful village. Perfectly positioned to explore the surrounding area.

  • Leo

    We had a great stay here over the August Bank Holiday. The Matchbox is beautifully decorated with lots of lovely features, and is ideally located for day trips into Rye and the surrounding areas.

  • Michelle

    Hi we stayed at the Matchbox cottage for a week, the property and location was beautiful. We came home so relaxed we would definitely recommend it. Plus Jacqui was a wonderful host. We will definitely be re-booking for next year.

  • Sandra

    Very comfortable cottage furnished to a high spec. Perfect location for exploring East Sussex. Jacqui is an excellent host who provided all the information we needed to make our stay so enjoyable. Very comfy beds! Would highly recommend lunch at The Swan, Chapel Down vineyard. The highlight of our stay. The New Inn in Winchelsea also provided good hearty pub food.

  • Linda

    Lovely clean well equipped cottage located centrally in Winchelsea.

  • Tim

    A beautiful and comfortable house in a very special location.

  • Grant

    Beautiful small house, tastefully, yet comfortably decorated. Lovely furnishings and bed linen, we had a very comfortable stay. Would certainly recommend for the local beaches and walks.

  • Thomas

    We loved the house and all the great art and drawings in every room

  • Julie

    Lovely comfortable house in a great spot!

  • Sarah and Steve

    One bright and sunny weekend in February we were lucky enough to stay at Matchbox situated in Winchelsea opposite a beautiful church and next to a great little shop. The house itself is gorgeous, it's artsy and has lots of character with its quirky steep staircase and slightly unconventional layout. It has 2 comfy beds with fresh smelling linen, spotless bathrooms and a cute kitchen that has all amenities. The second I walked in I felt at home, it's an absolute perfect location for exploring the local area being only a few mins drive to the beach, and to neighbouring Rye. Our visit to Winchelsea and Rye was idyllic with it's independent shops and tastey restaurants, it was like stepping back in time before big supermarket chains and department stores took over the world, everyone was so pleasant. We had such a great stay. We'll definitely visit again and next time explore Hastings. 😊

  • Penny

    Accuracy -good ( perhaps stairs might be too steep for some ) Check in- very good Cleanliness- very good Communications- very good Location- very good Value- good Positive- lovely cottage great position and next to great village shop open 7 days a week- great interior with lovely art work Negative- none for us - stairs steep for some - my sister and I are both over 70 years old and found stairs ok Stars 5 stars All good - great accommodation and easy to book

  • Derek and Angela

    Wow what a lovely unique cottage.......everything you need for a lovely stay and with fantastic shop next door to serve all your needs. Winchelsea is a quaint little village with plenty of history and with great dog walks on your doorstep. Matchbox serves all your needs. Highly recommended and we look forward to returning.....well we can only give it 5 stars but would have given 6 if we could!!!!!

  • Sally & Gary

    Thank you for our stay at Matchbox, we really enjoyed it and it enabled us to stay really close to family and have some invaluable time together, which we will be eternally grateful for. The property was very clean and tidy, is decorated to a high standard and was just as we expected. Our only feedback would be that although the duvets are very beautiful they are incredibly thick for this time of year and we were all melting, but without using them we were cold so felt we had to continue with them: even a flat sheet under the duvet would’ve been a great help so we could’ve used that if not a thinner duvet. The first floor bedroom mattress is also a little unusual in that it seems to sink at the sides and rise in the middle, this is the same as our experience a couple of years ago. Many thanks for excellent communication and a great stay,

  • Vicki

    Amazing property. High spec and beautiful artwork. A real home from home. Winchelsea is a beautiful village and a great base for walking and exploring the area.

From £86 - 350/Night