As you drive through the gates and along the gentle curves of the drive, the scene is set for a rather special experience. The Paddock Cottage forms one end of the low red brick building on your right-hand side as you enter the courtyard. The other end is its sister holiday let, Chestnut Cottage. This lovely retreat is surrounded by beautiful countryside yet only a mile from Winchcombe and Sudeley Castle and Gardens.
Compact and bijou, yet with everything you could possibly need, Paddock Cottage has been stylishly and thoughtfully designed to maximise the space available. Pale shades of green, yellow, and blue create a calm and relaxing space, whilst the modern furnishings bring a sense of urban luxe to this rural retreat. The open-plan living area has a well-equipped kitchenette and a plump, comfy sofa, creating a cosy place to relax. There's a sunny bedroom with double doors to a private patio and the smart shower room features dark green tiles and a corner shower.
To the rear of Paddock Cottage lies the field which gives rise to its name. A private enclosed patio furnished with a table and chairs overlooks this peaceful expanse of green. Linger for a while and listen to the sound of the birds in the trees, watch the sunsets and enjoy meals prepared on the charcoal barbecue.
*Dogs: 1 well-behaved dog welcome at the cottage at an additional cost each. Please let us know if you will be bringing a dog and we will then revise your booking confirmation. The pet fee is NOT included in your booking fee. A request for an additional fee per pet will be sent to you after you have placed your booking. Your pet fee must be paid for before your arrival date.
Ground Floor
Entrance Hall: Leave muddy wellies outside on the wrought iron boot stand before stepping through the front door into Paddock Cottage. The small entrance hall houses a shoe rack and coat hooks for outdoor gear.
Kitchen/Living Room: This well thought out space has a well-equipped kitchen area complete with a washer-dryer, slimline dishwasher, microwave-combi oven, and a two-ring induction hob. The pale grey units are topped with wooden work surfaces creating a modern, yet rustic feel. A large window overlooks the courtyard and allows plenty of natural light. The rest of the space creates a welcoming living area with a plump sofa, large Smart TV and large window overlooking the green swathe of paddock beyond.
Bedroom: This pretty bedroom has a gentle woodland feel with a William Morris bedspread on the double bed and tree silhouettes on both the pendant lampshade and reading lamps that sit on the bedside tables. The botanical prints and artwork, further enhance the nature-based design. Cosy rugs sit on either side of the bed for keeping toes toasty and a stylish wood hanging rail provides space for hanging clothes. A pale wooden dressing table with a large mirror and a plush stool sits on one side of the double doors, which lead out to a private patio. It's a lovely place to enjoy lazy mornings as the sun creeps across the field in front of you.
Shower Room: This smart shower room features dark, charcoal grey tiles underfoot and fabulous dark green wall tiles. The corner shower makes great use of the space as does the vanity unit which has a hand basin with storage underneath. There's also a W.C, wall mirror and frosted window which lets in the natural night.Outside The private enclosed patio overlooks the tree-lined paddock. It's a peaceful spot to enjoy a barbecue or just relax and soak up the sounds of the countryside. There is parking for two cars in the courtyard at the front of the cottage.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Cheltenham
Located in Cheltenham, this cottage is in a rural area. Cheltenham Town Hall and Sudeley Castle are local landmarks, and some of the area's attractions include Toddington Narrow Gauge Railway and Gloucestershire Warwickshire Railway. Travelling with kids? Consider Parabola Arts Centre and Walks With Hawks.
St Peter's Church Winchcombe - 5 min drive - 2.4 km
Belas Knap - 6 min drive - 2.7 km
Winchcombe Folk and Police Museum - 6 min drive - 2.7 km
Cheltenham Racecourse - 16 min drive - 12.0 km
Cheltenham Town Hall - 21 min drive - 15.4 km
Getting around
Toddington Railway Station - 16 min drive
Oxford (OXF) - 76 min drive
Restaurants
Costa Coffee - 10 min drive
Kings Arms Prestbury - 8 min drive
The King's Head - 9 min drive
Costa Coffee - 10 min drive
The Royal Oak - 10 min drive
Frequently asked questions
Is Paddock Cottage - sleeps 2 guests in 1 bedroom pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Paddock Cottage - sleeps 2 guests in 1 bedroom?
As of 30 May 2026, prices found for a 1-night stay for 2 adults at Paddock Cottage - sleeps 2 guests in 1 bedroom on 6 Sept 2026 start from AU$325, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Paddock Cottage - sleeps 2 guests in 1 bedroom?
On-site parking is available at the property.
What time is check-in at Paddock Cottage - sleeps 2 guests in 1 bedroom?
Check-in begins at 4:00 PM.
What time is check-out at Paddock Cottage - sleeps 2 guests in 1 bedroom?
Checkout is at 10:00 AM.
Where is Paddock Cottage - sleeps 2 guests in 1 bedroom located?
This family-friendly Cheltenham cottage is located in a rural location, within 1 mi (2 km) of St Peter's Church Winchcombe, Winchcombe Folk and Police Museum and Belas Knap. Sudeley Castle and Prescott Speed Hill Climb are also within 3 miles (5 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Great location and very easy access to local village, shops and restaurants. We stayed for 5 days to attend the Cheltenham Horse Racing Festival and the ease of access to racecourse using local taxis was perfect. Lindsey is on hand to advise and resolve any problems, she even arranged the transport of a bag we left behind! Imagine this would be an ideal location for walking and sight seeing the Cotswolds!
Peter S.
Stayed 5 nights in Mar 2026
From a partner site
10/10 Excellent
8 Nov 2025
Paddock
Peaceful and comfortable cottage with friendly and helpful managers. Peaceful and comfortable cottage with friendly and helpful managers.
From a partner site
10/10 Excellent
Jana B.
3 June 2024
Wonderful place to be!
The Cottage is really wonderfull, also the garden and the village with little shops and restaurants is nearby, We would love to come back!
Jana B.
From a partner site
10/10 Excellent
Teresa H.
14 Oct 2025
Excell
We had an absolutely delightful stay at Paddock Cottage, the cottage is very well equipped and very comfortable, I would happily stay here again, the local area is stunning! Perfect for a short break or a longer stay!
Teresa H.
From a partner site
10/10 Excellent
Dawn W.
3 Aug 2022
Lovely quiet location
Perfect location for couples to visit attractions in the Cotswolds. We stayed here to visit Sudeley Castle which was brilliant. The accommodation was furnished to a high standard and very comfortable.
Dawn W.
Response from VrboOwner on 8 Aug 2022
Hi Dawn, Thank you for your lovely review, which we have passed on to the owners. We hope you will return to stay here or at one of our other properties. Best wishes, Bolthole Retreats
From a partner site
10/10 Excellent
17 July 2024
Perfect stay
Paddock Cottage is a lovely cosy cottage. Beautifully clean, decorated with some lovely touches to give it a homely feel.
Set in lovely grounds in a good location for exploring the Cotswolds.
From a partner site
10/10 Excellent
23 Oct 2023
Lovely Stay
We had a lovely stay at Paddock Cottage for a few nights! The weather was a bit rainy and the cottage was perfect to get dried off and warm! Really nice decor and amenities and perfect for us with our Spaniel
quiet and relaxing cottage with everything you need for a stay. close to great nearby activities. and took advantage of the walking trails also.
Susan M.
Stayed 6 nights in May 2024
From a partner site
10/10 Excellent
2 July 2025
Great Location
We had a lovely stay in Paddock Cottage. Located in a peaceful area. Everything provided that you would need.
Would have been good to of had a clothes horse as certain clothes I didn’t want to tumble dry.
Response from VrboOwner on 3 July 2025
Thank you for taking the time to share your thoughts with us on your recent stay at Paddock Cottage. We’re delighted to hear that you enjoyed your stay. Your valuable feedback regarding having a clothes horse has been shared with the owner who has taken this onboard and it is being looked into. We hope to see you in the Cotswolds again soon.
From a partner site
10/10 Excellent
7 July 2025
Beautiful Cottage
We loved the Paddock cottage it met all of our needs. The one comment I will make is that if you did need to use the washing machine there didn’t seem to be anywhere to hang your washing up, this is just an observation not a criticism.
Response from VrboOwner on 9 July 2025
Thank you for taking the time to share your thoughts with us on your recent stay at Paddock Cottage. We’re delighted to hear that you enjoyed your stay. Your feedback is much appreciated and has been shared with the owner, who let us know that there is a clothes rail available for hanging washing. They would have been more than happy to point you in the right direction if you had contacted them. We hope to see you in the Cotswolds again soon.
From a partner site
8/10 Good
2 July 2024
Great stay
Absolutely stunning cottage, perfect for mini getaway. The only issue was the directions, on google maps you have to type "chestnut cottage", otherwise you are directed to the wrong location. Apart from that, would highly recommend this cottage.
Response from VrboOwner on 4 July 2024
Thank you so much for your review on your recent stay at Paddock Cottage, we are pleased to hear you had a great stay. We are however sorry to learn you had trouble finding the cottage, we would recommend using the written directions or the What Three Words which are sent 7 days before arrival date.
From a partner site
8/10 Good
Alan B.
25 Sept 2023
Everything there that we needed for a weekend away to a wedding.we had a great outlook
We had a great vista and lots of wildlife squirrels bring in abundance. There was everything in the cottage you would need for a short break of even a week away.
Alan B.
From a partner site
10/10 Excellent
30 July 2024
Lovely cottage for long weekend
We found the perfect spot halfway our walking tour trough the Cotswold to rest for a couple of days. Lovely cottage, everything you need is there. Nice and clean. Quiet and peacefull environment.
From a partner site
10/10 Excellent
16 Sept 2025
Wonderful holiday hideaway
We had a wonderful much needed holiday at Paddock Cottage.Although in an out of the way place, it was easy to find thanks to great directions from the owners.The cottage was very clean, comfortable and beautifully furnished.A welcoming bottle of fizz and some milk was a lovely welcoming surprise.Winchcombe is the perfect place from which to explore, with so many lovely places within easy travel distance.It was hard adjusting back to congestion and busy pace of everyday life after the peace and charm of the Cotswalds.
From a partner site
10/10 Excellent
Debbie H.
26 Mar 2025
Paddock Cottage Review
Thank you to the owners of Paddock Cottage and Bolthole Retreats. The process was very professional from start to finish. The Cottage itself was fabulous. Very good location, great bed and shower. Sofa and TV was perfect. The kitchen had everything you needed. The Cottage is in great condition and we enjoyed our stay. We will return.
Debbie H.
From a partner site
10/10 Excellent
2 Aug 2024
Beautiful high end cottage stay
Lovely spacious top notch cottage out in the countryside, very peaceful and quiet. Plenty of parking, living area way bigger than it looks in the photos and everything you might need is available. Was delighted with the heavy curtains in the bedroom ensuring we weren’t awoken by the sun at the crack of dawn. Beautiful property, just a shame we were out for most of our stay and didn’t enjoy it as much as we would’ve liked to.
From a partner site
10/10 Excellent
13 Oct 2023
Perfect cottage for two
This is a lovely cottage, perfect for a short stay. It's very clean, comfortable and well appointed. It's in a peaceful location which meant we had quiet nights and undisturbed sleep.
The only slight issue I had was with the overhead shower because I don't like having to wash and style my hair every day. A height adjustable shower would have been perfect. And no, a shower cap is not the answer.
From a partner site
8/10 Good
27 June 2022
Paddock Cottage
Overall the property was very comfortable and we enjoyed our stay. However, we were unable to connect to the internet when we arrived. We rang the number we had been given and then sent a message but received no reply. in the morning we rang Bolthole Retreats who gave us a different number. This resulted in a partial coverage but we were not able to use the smart tv while staying at the property.
There were only two mugs at the property, although there were lots of glasses.
Response from VrboOwner on 1 July 2022
Thank you for your review.
We are glad that you found the property comfortable and that you enjoyed your stay regardless of the initial difficulty in connecting to the internet. The owner will look at the Smart TV and will also supply more mugs to the property.
We hope that we can welcome you back to The Cotswolds in the future.
From a partner site
10/10 Excellent
4 Nov 2022
Excellent cottage!
Lovely cosy cottage, perfect for a quiet birthday celebration. Ideal for those wanting to bag the highest point in Gloucestershire at nearby Cleeve Common.
From a partner site
10/10 Excellent
4 July 2022
Excellent weekend stay in lovely location and cottage
A great, clean and lovely retreat for two people in a beautiful setting. The location is great and very close to some wonderful little villages including within walking distance of Winchcombe. The Winchcombe way offers as much walking as desired and across beautiful scenery ending up wherever you fancy. A wonderful place to stay!
From a partner site
10/10 Excellent
26 June 2022
Would definitely book again.
In the area for work, originally booked somewhere more basic but husband was able to come with me so decided to look for somewhere a bit nicer - definitely lucky to find Paddock Cottage! Not the largest of places, but didn't feel cramped at all and had everything we needed for a comfortable weekend stay; we both thought that the cottage would provide a good place to stay for a longer period of time, too. If I need to stay in the area next year, we'll definitely look to re-book.
From a partner site
10/10 Excellent
18 Mar 2022
Beautiful cottage in a peaceful location
I stayed here during Cheltenham Festival week. It was like an oasis to get back to after a busy day at the racecourse. Everything you need is provided.
From a partner site
10/10 Excellent
sarah h.
14 Mar 2022
Lovely stay in A* accommodation!
We loved Paddock Cottage - sparkling clean, amazing views of the surrounding countryside, warm and welcoming and beautiful decor. Comfy bed too! The paddock at the back of the cottage was also brilliant for walking and playing with our dog. Loads to see and do locally, Winchcombe is a gem of a town! Highly recommended, hope to return.
sarah h.
About the host
Hosted by Bolthole Retreats
What makes this property unique
Hidden behind a gated drive on the edge of Winchcombe, an ancient market town, Paddock Cottage is a bijou hideaway just for two. The traditional red brick exterior hides a thoughtfully designed space, which provides every creature comfort whilst the clean lines and stylish furnishings ensure this cottage feels light and airy. There's a spacious bedroom, an open plan living and kitchen area and a private patio to the rear, overlooking a tree-lined paddock. It's the perfect place from which to explore the north Cotswolds, the delights of Regency Cheltenham and enjoy exceptional walks.
Languages:
English
Premier Host
They consistently provide great experiences for their guests