Chestnut Cottage
The simple and traditional red brick exterior of Chestnut Cottage hides a beautifully stylish and modern interior, where contemporary styling and thoughtful furnishings have created a sophisticated and welcoming rural retreat. Lying in the beautiful countryside within walking distance of Winchcombe’s medieval charms, this delightful property sleeps four guests in two spacious king-size bedrooms. With a fabulous bathroom including a standalone bathtub, plenty of parking and a peaceful terrace to the rear, this is the perfect place from which to explore the Cotswolds.
Overview
Surrounded by trees and the sound of birdsong, with gently rolling hills in the background, Chestnut Cottage offers a stylish place to stay within walking distance of Winchcombe. As you turn off the main road onto the tiny tree-lined country lane, the scene is set perfectly for your stay.
The entrance door leads into a long hallway, which runs in both directions, the wooden flooring creates a warm feel and multiple windows let in plenty of natural light. There are two spacious king-size bedrooms, with windows overlooking a green paddock to the rear, a beautiful bathroom with a double-ended bathtub, perfect for lazy bubble-filled soaks and a large, separate shower, plus a sunny kitchen-diner and a living room, with double doors out to a private patio.
Outside there is an enclosed private patio, with an access gate into the large paddock, surrounded by trees. Enjoy relaxed meals from the barbecue and soak up the rural landscape that surrounds you. The owners have rescue hens and lovely fresh eggs will often be available to purchase from an honesty box.
Ground Floor
Entrance Hall:
The long entrance hall runs in both directions from the front door with a wooden floor underfoot and plenty of windows letting in natural light. The natural lay of the land is sloping and the hall is multi-level, with two steps down towards the bathroom, two steps up to one of the bedrooms and two further steps up to the living areas. A long full-length mirror hangs at one end and the walls are lined with cupboards, providing useful storage.
Kitchen/Diner:
This bright, sunny room has a warm wooden floor, windows looking out to the courtyard at the front and paddock to the rear and has everything you need to prepare delicious meals. The well-equipped kitchen includes a range of built-in appliances with a washer-dryer, dishwasher and fridge with a small freezer box hidden neatly behind the smooth grey cupboard doors. A traditional butlers sink is set beneath the window looking out over the countryside beyond. The round wooden dining table seats four comfortably and is a cosy spot for sunny breakfasts and relaxed evening meals.
Living Room:
From the kitchen, there is a door into the living room, which is a light and airy space with windows on two sides and double doors out to the private patio. Bright pops of colour come from the two velvet sofas, one cobalt blue, the other moss green and a honey-hued rug covering the wooden floor. There’s further seating with a mid-century leather chair set by the patio doors. Industrial style shelving highlights the rural, yet modern feel as does the stylish wall mirror, lighting, circular glass coffee table and wooden TV unit which houses the smart TV.
Bedroom One:
With a super-soft carpet on the floor and a comfortable king-size bed, strewn with woollen cushions and a William Morris design bedspread, this spacious room is warm and inviting. Beautiful rural views add to the feeling of calm and a glass pendant light adds a touch of glamour. Twin bedside tables stand on either side of the bed with reading lamps and storage comes in the form of a chest of drawers. There are also three hanging hooks on the wall and further storage can be found in the hallway cupboards.
Bedroom Two:
Boasting the same lovely rural views as bedroom one, this is a beautifully light and spacious room. The king-size bed has a William Morris bedspread and print cushions and two bedside tables with on-trend pineapple reading lamps sitting on either side. There’s a chest of drawers, a dressing table and two hanging hooks, plus a wardrobe with hanging space can be found in the hall opposite the bedroom door.
Bathroom/Shower Room:
After a day tramping through the countryside retreat to this stylish and spacious bathroom, pour a glass of something chilled, fill the standalone bathtub with bubbles and relax. There’s also a separate rainfall shower, WC, and a vanity unit with a handbasin and a well-lit mirror.
Outside
To the rear of the property, accessed through the double patio doors in the living room there is a private patio, enclosed by a picket fence and overlooking a grassy, tree-lined paddock. Guests are welcome to enjoy this space and there is an access gate from your patio. There’s a wooden table and bench-style seating, perfect for alfresco meals or simply enjoying a drink as you soak up the countryside views around you. A charcoal barbecue is also provided and there is parking for two/three cars in the courtyard at the front of the cottage.
Facilities
Indoor
Bedroom One - King-size
Bedroom Two - King-size
1 Bathroom - Family Bathroom With Standalone Bathtub And Separate Shower Cubicle
Hairdryer - 2
Oven
Hob
Microwave
Toaster
Kettle
Fridge
Freezer - Compartment In Fridge
Coffee Machine - Nespresso
Dishwasher
Dining Table - Seats 4
Washing Machine
Tumble Dryer
Iron
WiFi *Please Note That Speeds Are For Guidance Only And Are Not Guaranteed - 12-24 Mbps
TV - Smart
Board Games
Travel Cot (cot Linen Not Provided)
Highchair
Outdoor
Dog Friendly - 1 Well-behaved Dog Is Welcome For An Additional Fee
Garden - Fully Enclosed
Outdoor Dining Area
BBQ - Please Provide Your Own Charcoal
Parking - Off-road Parking For 2 Cars
On your Doorstep
The historic town of Winchcombe has a small Co-Op and a Morrisons Daily for your everyday needs. You will also find Vale and Hills butchers, a florist, North’s Bakery and a deli at William’s of Winchcombe. Just outside Winchcombe, Hayles Fruit Farm (3.5 miles) offers a fabulous selection if pick your own depending on the season and has a farm shop and café on site which is popular with walkers in the area.
Eating Out
- The Lion Inn, Winchcombe – classic pub food served in beautifully historic surroundings (1 mile)
- Restaurant 5 North Street, Winchcombe – exquisite food prepared by a passionate chef with a fantastic reputation (1 mile)
- The Mount Inn, Stanton – far-reaching views accompany your meals and drinks at this rural country pub (6 miles)
- The Ivy, Cheltenham – the perfect choice for sophisticated dining in a stunning location (8 miles)
Walks
Winchcombe’s rolling countryside is a true walkers’ paradise, with plenty of options for casual, seasoned, and hardy walkers. Winchcombe itself is a “walkers are welcome” town, a special status awarded to towns and villages which go above and beyond with their walking amenities, making it a fantastic destination for groups in search of a walking break. The small lane leading to the entrance to Postlip House is also a public footpath that leads to the Cotswold Way and Winchcombe. Turn right out of the black double gates until you come to the River Isbourne. At the river, turn left and follow the footpath to a local road junction. Follow this road to the right. You will shortly come to the Cotswold Way which takes you into Winchcombe and joins with the Winchcombe Way. Trace your footsteps back or make a large loop eventually back to Postlip House Cottages via a combination of the Winchcombe Way, Cotswold Way, and local footpaths.
Places to Visit
- Gloucestershire Warwickshire Steam Railway, Winchcombe – journey through the Cotswolds on a steam train taking in the countryside views (2 miles)
- Hailes Abbey, Hailes – ruins of a medieval abbey with a museum telling its history (3 miles)
- Cotswold Farm Park, Guiting Power – a popular day out for families to meet the rare farm breeds (7.5 miles)
- Broadway Tower, Broadway – enjoy the fabulous views from this iconic landmark and visit the café during your time here (9 miles)
- Train - Cheltenham Spa railway station (7.7 miles) has regular services from London Paddington as well as the north and west of England.
- Taxis - Cleeveline Taxis; Abbey Private Hire
Points of Note
This property has a check-in time of 16:00 and a check-out time of 10:00
- Book with us to get exclusive discounts to top attractions and experiences..
- 1 well-behaved dog is permitted at Chestnut Cottage for an additional fee.
- Chestnut Cottage is split level with two steps down to the bathroom, two steps up to the second bedroom and two further steps up to the kitchen/dining area and living room.
Check Availability
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Handpicked by us
Why we love this
- Just a 10-minute walk from the ancient town of Winchcombe, which offers a wide selection of restaurants, pubs and cafes,
- The Regency spa town of Cheltenham is 6 miles in the other direction
- The walking trails of Cleeve Hill, the Cotswold Way and the Winchcombe Way are right on your doorstep.
Discover more
The Location
Chestnut Cottage has a peaceful location just a 10-minute walk from the ancient town of Winchcombe, which offers a wide selection of restaurants, pubs and cafes, and the Sudeley Castle Estate. The Regency spa town of Cheltenham is 6 miles in the other direction. The walking trails of Cleeve Hill are on your doorstep as is the Cotswold Way and the Winchcombe Way.
And relax..
Why book with us
1.
Guaranteed
best price
Book your holiday home directly with us for the best possible price. Because we work exclusively with our owners; we guarantee you won’t find our properties cheaper elsewhere.
2.
Guaranteed
best price
Book your holiday home directly with us for the best possible price. Because we work exclusively with our owners; we guarantee you won’t find our properties cheaper elsewhere.
3.
Guaranteed
best price
Book your holiday home directly with us for the best possible price. Because we work exclusively with our owners; we guarantee you won’t find our properties cheaper elsewhere.
Read our reviews
Cotswold paradise
Fantastic cottage beautiful decoration brilliant location everything as we expected and more pulled out all the stops
Debra Jones
Fantastic cottage, beautiful decoration, brilliant location, everything as we expected and more, pulled out all the stops.
Debra
Beautiful barn in a great location
We really enjoyed our stay in Chestnut cottage. Beautiful barn in a wonderful setting. The barn was well equipped and very comfortable. Great location with lovely walks.
Tom Lonergan
We really enjoyed our stay in Chestnut Cottage in Winchcombe. Beautiful conversion in a beautiful setting. Everything we needed was on hand. Will definitely be returning.
Tom
Excellent in every way
Have visited many times - always delightful! Clean, comfortable, well-appointed - great for the dog!
Rosanne Musgrave
Fabulous property, great communication and good pricing.
Judith
Have visited many times - always delightful! Clean, comfortable, well-appointed - great for the dog!
Rosanne
A lovely cottage to stay in for a weekend or longer and in a great location
We were two couples staying here for a long weekend and the property is perfect for this with ample parking for two cars. It is in a quiet rural setting but with easy access to nearby towns and places to visit.
The condition of the whole cottage and its contents was perfect and extremely clean. The beds are comfortable and in spacious rooms. The bathroom is also very spacious and the facilities excellent The kitchen has all the appliances that are needed and the bottle of bubbly in the fridge was much appreciated. One suggestion would be to have a few more plates and some serving dishes - we had to wash bowls half way through our meal.
Cathy Milne
Great stay and location while exploring the Cotswolds
Lovely cottage that has everything you need.
Comfy bed, fantastic shower and bath.
The secure outside space and the field for the dogs was great!
Would highly recommend!
Only negative was the sofas weren't very comfy.
Andrea Hough
Chestnut cottage stay May 2025
We stayed at Chesnut cottage in May 2025 for three nights. We found the property and location perfect. It was on the outskirts of Winchcombe with an easy 15 minutes stroll to the village. The Cotswolds way is nearby and plenty of walks from the cottage.
David Beaumont
We stayed at Chestnut Cottage in May 2025 for three nights. We found the property and location perfect. It was on the outskirts of Winchcombe with an easy 15 minutes stroll to the village. The Cotswolds Way is nearby and plenty of walks from the cottage.
David
Beautiful cottage excellently maintained
Comfortable and well equipped - ideal for a short stay - excellently maintained. Convenient parking.
Rosanne Musgrave
Quiet and peaceful
One of the best holiday cottages we have stayed in (we have stayed in over 25) recommended in every way,easy walk to Winchcombe by footpath or road in 15 minutes
Robin Horner
A beautiful stylish cottage
We found Chestnut Cottage to be a delightful place to stay. Both the cottage and grounds were beautiful and well maintained.
Guest
Very well thought out
You can tell these owners have put a lot of thought into making this the best experience. The decor is lovely and, whereas many cottages only put in the absolute basics, the attention to detail with all the appliances, storage and soft furnishings is much better here. Even the hairdryer was good quality; something you can rarely count on when you go away. The location is fabulous, just a lovely short walk into Winchcombe to a dog-friendly pub, our pup absolutely loved his holiday. The only very minor things to mention were that the window on the far side of the cottage seemed to have a failed seal and lots of flies were getting in, but we were able to cover it up for the duration of our stay easily enough. We also couldn’t seem to find a clothes horse (although we may not have been looking hard enough) and that would have been useful for things that were not tumble dryer friendly, but the heated towel rail helped a lot. The bathroom especially was absolutely lovely. All in all a wonderful experience
Rosalind Gillman
Excellent Stay
We loved Chestnut Cottage. We had a lovely 4 nights. The property is beautifully decorated, homely and in a great location. Great walks and a good field for our dog. We would definitely recommend and would really love to return. We can’t fault anything!
Caroline Thomas
A fabulous break
Met up with my friend for a week at Chesnut Cottage and we absolutely loved it. The house is very spacious and very well presented and had everything we needed. The location is fabulous - so quiet but equally so close to everything. The whole experience from booking to leaving at the end of the holiday was smooth and issue free. We will definitely be returning!
Terri Turton
The perfect retreat!
Chestnut Cottage was perfect in every way! We loved our stay and everything about it exceeded our expectations! It is lovely to have luxury dog friendly accommodation. With walks straight from the cottage, we hardly used our car for the whole week. We will definitely book with Bolthole Retreats again and recommend to friends and family.
Sue McNeilly
Lovely weekend, gorgeous cottage
Chestnut cottage was absolutely delightful. Was of a very high standard and very well equipped. We had booked for a long weekend to attend the Fantasy Forest Festival at Sudely Castle. The location of the cottage was excellent and very private. The cleanliness was first class. The kitchen was very well equipped. The bathroom was superb and made me have "bathroom envy". The furnishing were of top quality and the owners had put a lot of effort into even the smallest of details to make the cottage feel luxurious as well as cosy and welcoming. I would definitely stay at Chestnut Cottage again and would highly recommend.
Belinda Allan
Excellent accommodation
The accommodation was in very good order, spacious and well appointed. As walkers the property was well located about 1 mile from the centre of Winchcombe. We wouldn't hesitate to recommend this property to friends .
Paul Hunter
Peaceful Retreat
Generally all round very accommodating. Lovely farm eggs, good parking. Lovely peaceful atmosphere. Only complaint is you need to update your TV software, Lots of channels weren't on the TV. It didn't spoil the holiday.
Jennifer Mundy
Wonderful stay at Chestnut Cottage
We had an excellent long weekend stay at Chestnut Cottage. The property was lovely, with no expense spared on the interior and the amenities there.
The location was also great, and within easy reach of nearby places such as Winchcombe and Cheltenham.
The hosts were also available when needed, with help given straight away when struggling with the entry code.
Would definitely recommend.
Richard Thompson-Cozens
We’ll appointed, comfortable Cotswolds cottage
Very helpful and charming owners - everything provided and of excellent quality - we’ve stayed before and will definitely come again… thank you!
Rosanne Musgrave
Beautiful cottage great location
Absolutely stunning cottage, immaculate in every way! Felt like I was in a homes and gardens magazine! Spotlessly clean, beautiful decor and had everything you could possibly need.
Olivia Ward
Overall Fantastic Cottage
Location - Great
High end kitchen items
Beds - comfy
Cleanliness - Fantastic
Wifi - poor (router was down the hallway other end if the living room and kept loosing connection for the advertised Smart TV.
Sofa - needs to be a high back ideally
Would recommended and would book again.
Sarah Powell
Idyllic
A beautiful home from home in a peaceful setting. Everything about Chestnut Cottage felt luxurious. The bath and shower are huge, and the beds are so comfortable.
Sophie Ward
Chestnut Cottage - Winchcombe
The property is absolutely gorgeous (and I'm fussy). All finished to a high spec. The bed was super comfortable with luxurious bedding. The grounds and setting was so relaxing. Winchcombe is a gem - absolutely delightful. I loved it all and will return.
Christina Bell
Fantastic week
A truly amazing week!!
The cottage was delightful, extremely well furnished and equipped, beds amazedly comfortable and a stunning location. The owners were so helpful as was the gardener.
Was sorry to leave but will be back at some point.
Sue for Sussex and Bev from Canada.
Susan Barker
Relaxing stay at Chestnut Cottage
We enjoyed our stay in this cosy ,well equipped and peaceful cottage in the Cotswolds.The cottage is in a great location for walks,visiting Winchcombe,Sudeley castle and the local preserved railway.We would recommend it to anyone wanting a relaxing and peaceful holiday.
Susan Fishman
Stunning Property in remote location
My friend and I spent just under a week at Chestnut cottage… was an absolutely lovely experience… if you are looking for a remote getaway in a stunning setting then this is the place… lots of little luxuries and the property is finished to really high specification…
The bathroom was my favourite room and I spent a lot of time in there!
My only suggestion would be to have some cleaning products for the guests as there was only washing up liquid, but surface spray, bleach, hoover would be appreciated… although the owners did let me use a hoover upon request…
We also had a problem with the hot water on one of the days and the owners were straight over to help and the problem was fixed and plumber was out straight away so felt really supported during our stay…
Would definitely recommend… thank you so much for a lovely stay x
Charlotte Voller
Very nice stay
Very nice accommodation. It had a great filed for children and dog to play in. Only thing of note is that there is a small stretch of road (approx 0.3 miles) that has no pavement if you wanted to walk into town. We made it work but might be an issue for some.
Nicholas Harston
Beautiful stay
We had a lovely stay at the cottage. The only thing that could be improved is signage. We went down the wrong turning as we followed the satnav and it added about an hour on our drive! As it was all back roads, cows and sheep! No signage. If there was a sign at the entrance of the road it would have saved a lot of stress. The cottage is great, warm and cosy. Beautiful surroundings. The bathroom is amazing with underfloor heating. To eat you need to drive. So I wouldn't recommend it if you were hoping to travel there by train unless you didn't mind taxis to supermarkets or pubs, ect. We would stay again.
Isabella Bullock
Beautiful property
Beautiful property in a lovely peaceful location close to the Cotswolds and all it has to offer. Shame it rained for us!
Karen Jones
Lovely
A beautifully presented cottage in a great location. Very enjoyable stay in a very beautiful part of the world
Cheryl Kay
Great place to stay
Would highly recommend. The property is finished to a high standard very clean and well maintained. Our only constructive feedback would be to have a hoover in the property, we have two young children so it would have been great to be able to clean up a bit more ourselves.
Aidan Wood
Comfortable and well appointed
An excellent short stay with helpful owners/ housekeeper- quiet and relaxing. Will definitely return!
Rosanne Musgrave
Chestnut Cottage Review
What a wonderful place to stay - we were amazed at the standard of this accoommodation - the quality of everything was excellent. The owners had thought of everything that you might need during your stay - there had been no short cuts. We will certainly be coming back - thank you.
Sharon Quigley
A gem in the Cotswolds
Chestnut Cottage is one of 3 cottages located within the grounds of Postlip House. The grounds are quintessential English country house and are beautifully maintained. This follows through to the cottages. Chestnut Cottage was decorated and furnished to a very high standard, with quality fixtures and fittings. The 2 bedrooms are very comfortably furnished, with the beds being super comfortable. The bathroom is gorgeous - a large shower and a wonderful freestanding bath. The kitchen has quality Siemens appliances and is well equipped for 4. Sitting room is very stylish in a mid century style. Outside is a substantial (heavy!) wooden table and chairs. The patio is paved and enclosed. Everything has been done to a high standard and I’d not hesitate to recommend it.
Winchcombe itself is a typical Cotswold market town with a good selection of shops and pubs. Recommend the White Hart Inn for food and service. It’s within walking distance but not on the main road as it’s quite busy. However, parking (in June) easy and cheap/free.
Karen Martin
Chestnut Cottage
Newly refurbished property, finished to a high standard. Stylishly and comfortably furnished. Quiet and peaceful area. Overlooks a large, fenced grass area at the back which is great for the dog. Excellent location to explore the Cotswolds. Only a short walk from Winchcombe. Lovely place to relax and unwind.
Guest
Create Memories
Experiences designed to make your stay unforgettable
We have curated not only a portfolio of properties, but also a portfolio of experiences we recommend everyone try the next time they visit the Cotswolds and surrounding counties. This selection of ours is constantly growing as we discover more hidden gems and local stars. Many of the experiences are incredibly popular, and we encourage booking in advance because these little extras can turn your everyday holiday into a fantastic, fond memory, one you aren’t soon to forget.
