Chestnut Cottage | Winchcombe, Cotswolds | Dog-Friendly
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Chestnut Cottage


Sleeps 4
Dog Friendly
Local Pub
12-24 Mbps
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.
Full Description
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.

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.


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.
Full List of Facilities


  • 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
  • Travel cot (cot linen not provided)
  • Highchair


  • 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
Supermarkets and Shopping:

Winchcombe has several food shops, including a Co-Operative Food store. Vale & Hills Family Butchers sells local meat, North’s Bakery sells a great selection of bread, pastries and baked goodies and Food Fanatics deli, wholefood store and café sells a wide range of speciality foods. For a larger or more varied shop, Tesco Superstore in Bishop’s Cleeve is just a 15-minute drive away, whilst Cheltenham’s impressive selection of stores, eateries and amenities are just a 20-minute journey away.

Eating Out:
  • The Corner Cupboard (0.7 miles)
  • The Lion Inn (1.1 miles)
  • 5 North Street (1.1 miles)

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:
  • Sudeley Castle (1.7 miles)
  • Cheltenham (7.2 miles)
  • Cotswold Farm Park (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
There is so much to see and discover in the Cotswolds, why not have a look at some of our favourite Bolthole Retreats Experiences.
Points of Note
  • 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.
Neighbouring Properties
Chestnut Cottage is one of three Postlip House Cottage holiday lets that can be booked with Paddock Cottage and The Hayloft for families or friends wanting to travel together but have their own space. You can share the properties between your group, but please bear in mind you would not have enough seating to sit/eat together.


Very helpful and charming owners. Everything was provided and of excellent quality. We've stayed before and will definitely come again,thank you!

| 16/11/2023

An absolutely stunning cottage, immaculate in every way! Felt like I was in a Homes and Gardens magazine! Spotlessly clean with beautiful decor and it had everything you could possibly need.

| 13/11/2023

The location was great. The kitchen is well equipped with high-end kitchen items. The beds were comfy and the cleanliness was fantastic. Would recommend it and would book again.

| 30/10/2023

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.

| 21/10/2023

The property is absolutely gorgeous and all finished to a high spec. The bed was super comfortable with luxurious bedding. The grounds and the setting were so relaxing. Winchcombe is a gem,absolutely delightful. I loved it all and will return.

| 03/10/2023


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.