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Lovely, cosy Cotswold retreat ideal for rural and romantic breaks



Updated: 05-Oct-2016
Central Winchcombe, Cotswolds England - 5 Minutes to Pubs, Shops, Country Walks

Lovely country retreat with a modern twist in the heart of this lovely, preserved, historic Cotswold town ideal for romantic breaks, walkers and small dogs; beautiful walking and cycling countryside; the Cotswold and Winchcombe Way paths pass through the town and Broadway, Bourton on the Water, Cirencester, Tewkesbury and Stratford-upon -Avon are all within 20 miles of the cottage. The cottage is well paced for Cheltenham Race Course and Sudeley Castle is 10 minutes walk.

  • Sleeps 2
  • 1 Bedroom
  • 1 Bathroom
  • Parking
  • Garden
  • Barbecue
  • Pets considered
  • Internet
  • Dish washer
  • Washing machine
  • Towels provided
  • Linens provided
  • Accept Credit Cards
  • Bookable online

Top Traveller Review

About the Owner

Carol and Jay are both country lovers and keen walkers who grew up in Worcestershire.

We have held a variety of jobs and have lived in different parts of the UK but rate the Cotswolds for its beauty and variety while being well-placed for transport links. We embarked on our property venture after a mutual friend's funeral and contemplating life ahead. We hope to build a small business as an alternative to the cut and thrust of city life as we get older. We think there is a gap in the market for small, deluxe cottages for couples or single people wanting a "home from home" but also the added comfort of all modern amenities. We have tried to create this atmosphere in our cottage as well as providing a romantic, ideal country bolt hole.

Speaks English

Guestbook comments from the owner

"We had a very good and enjoyable stay at Penny Cottage. My wife was impressed with the amount and variety of kitchen utensils, quality of glasses etc"

July 2014

"You have thought of everything we could possibly need during our stay and more. Thank you"

August 2014
Apr 2014
  • 1 of 1

18 Reviews

based on 18 holidaymaker reviews


Beautiful well located cottage

  • 5 of 5

We absolutely loved our stay in penny cottage. It was extremely well located, not only in the heart of Winchcombe but so easy to explore the lovely surrounding Cotswold areas. The cottage is gorgeous, very well equipped, extremely clean and beautifully done. It's also spacious for two (and rare to find this sort of accommodation just for two) with a lovely huge bathroom and kingsize bed! My husband loved the real fire which we used regularly. The owners were also thoughtful in providing disposable Bbq's for us, although weather meant we didn't use them in the end. We don't think the pictures do the cottage justice, it's even more lovely so just go and see it for yourselves! By the way, I am shocked by the one negative review here and think that must be someone with an axe to grind as this is a beautiful place, we travel a lot in uk and abroad and its one of our favourite places we have stayed. We really hope to return.

  • Review Submitted: Sep 21, 2016
  • Date of Stay: Sep 2016
  • Source: Owners Direct, from HomeAway
Owner's Response: We are so pleased Penny Cottage lived up to your expectations and would happily welcome you back. We have taken on board any previous criticisms however minor because we strive to provide top of the range accommodation especially for couples.
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Small Cottage

  • 3 of 5

Lovely cottage inside, spoilt by the outside space which needed tidying. Although their was a note to the effect the grass had not been cut due to wet weather the sitting area was not useable until the gardeners arrived on the Thursday. They swept away all the weeds moss and leaves. We left on the Friday!!

  • Review Submitted: Sep 14, 2016
  • Date of Stay: Aug 2016
  • Source: Owners Direct, from HomeAway
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Found the cottage to be home from home comfortable and well equiped with all mod cons.

  • 4 of 5

Lovely five day stay lovely walks smashing weather hoping to visit Winchcombe again and more of the Cotswolds.Thank you Carol and Jay.

  • Review Submitted: Aug 21, 2016
  • Date of Stay: Aug 2016
  • Source: Owners Direct, from HomeAway
Owner's Response: We are delighted you enjoyed your stay I. out cottage and appreciate how tidy you left it. We would be delighted to welcome you back to explore more of this lovely part of England. Jay and Carol
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  • 3 of 5

Lovely cottage in a beautiful location, but the cottage is in need of some TLC it needs a dam good clean and de-dogged?? As an asthma sufferer the strong smell of dogs and hair everywhere really spoiled our holiday! The entire cottage is in need of a good clean, the down stair carpets are a disgrace!! The garden is over grown with leaves from the winter all over the place, really untidy!! This is a lovely cottage just very poorly maintained?? Would like some of our money back please for payment for the cleaning we had to do.....

  • Review Submitted: Jul 28, 2016
  • Date of Stay: Jul 2016
  • Source: Owners Direct, from HomeAway
Owner's Response: In the light of so many previous positive reviews from non-dog owners and dog owners alike, we were concerned and surprised to read your comments, particularly as you had not raised any of these concerns with us during your stay. We do provide our telephone numbers and encourage all our guests to raise any issues as soon as possible after arrival. You gave us no opportunity to rectify the situation and we would have been happy to do so. The website clearly states that we accept well-behaved dogs and we query why you continued with your booking if dogs exacerbate your asthma. All our guests who bring dogs are very responsible and many leave the cottage spotless. Also, we do not accept that the carpets downstairs are "a disgrace". The front door leads directly onto the street and we work hard to ensure any mud, stains etc are promptly removed after each departure and throughly vacuum carpets and furniture. This is why we allow at least 4 hours for preparation and cleaning between departures and arrivals. Many of our returning guests have used the words "immaculate" to describe our cottage and it is therefore even more regrettable that the cottage did not meet your standards on this occasion. We accept that the garden is somewhat overgrown in places and you also arrived after a period of poor weather. On windy days, leaves do blow into our garden from the large tree next door. This is all part of country living but we have noted your observations. Our gardener was not always able to meet our requirements this year due to bad weather, but we are working on this to ensure that the main garden is kept as neat as possible for a holiday cottage. We were assured however that the patio and seating area were clean and tidy for your arrival. Thank you for your custom in any event but because you did not raise your concerns at the earliest opportunity and also stayed for the duration of the booked period, we do not propose to offer any refund. Jay and Carol
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1 1

Cosy cottage in the Cotswolds

  • 5 of 5

Such a wonderful cottage. It had everything I required - comfy bed, fabulous bathroom, well-equipped kitchen and a good sized dining room. All well presented and immaculately clean. The location was ideal for exploring the Cotswolds and surrounding area. My day at Sudeley Castle was great, and Stow on the Wold was a short drive away. This is the first time I have used Owners Direct and the booking was very straight forward. The owners contacted me swiftly, and responded to a couple of questions before I booked. It made me feel confident with going ahead with my short stay. I would love to go back to explore the area some more!

  • Review Submitted: Jul 20, 2016
  • Date of Stay: Jul 2016
  • Source: Owners Direct, from HomeAway
Owner's Response: Thank you for your resounding review. We work hard tto make our cottage like your a boutique hotel without other guests and your booking experience as hassle free as possible. Do come again Jay and Carol
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Great cottage in a great location...bags of charm for both

  • 5 of 5

Cozy,clean,well equipped, lovely garden, located close to everything in winchcombe, great shower,

  • Review Submitted: Jun 16, 2016
  • Date of Stay: Jun 2016
  • Source: Owners Direct, from HomeAway
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From the Owner

This is in an area of outstanding natural beauty as well as being well-located for the Cotswolds and Cheltenham Race Course, Oxford, Tewkesbury, Stratford- upon- Avon, Bristol, Gloucester and Worcester. All these towns are readily accessible and Winchcombe is very popular with walkers and cyclists, being on both the Cotswold and the Winchcombe Way. All paths are well sign-posted, offering gentle and steep country walks to suit all levels of experience and the surrounding countryside offers delightful unspoilt villages and pubs. The town is very historic and authentic and boasts at least 5 public houses, a Michelin starred restaurant within minutes of the cottage and a variety of cafes and interesting shops. The cottage is extremely well-placed for the Cheltenham racecourse as well as the Jazz and Literary festivals held in Cheltenham every year. It was chosen because it offers both country life as well as proximity to other pursuits.

Activity and Interests

Nearest Airport : Bristol or Birmingham at 30 Miles Nearest Barpub : The Lion pub at 100 Metres Nearest Golf : Winchcombe Hill at 0.5 Miles Nearest Train : Cheltenham at 8 Miles Nearest Restaurant : No 5 at 100 Metres Car: not necessary

Special interest holidays:

Walkers and cyclists welcome


Car useful but well served by buses to and from Cheltenham and Tewkesbury


Cheltenham 8 miles, Tewkesbury 6 miles

Further Details:

Michelin starred restaurant No 5 within 10 mins walk of property; excellent local pubs and antique shops

easy access to Cheltenham Race course; the place to be during Gold Cup week


Rental rates

Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
Winter 2016
1 Oct 2016 - 19 Dec 2016
3 night minimum stay
for 3 nights
Christmas/New Year 2016
23 Dec 2016 - 3 Jan 2017
3 night minimum stay
for 3 nights
10 Feb 2017 - 18 Feb 2017
2 night minimum stay
for 2 nights
Cheltenham Festival
10 Mar 2017 - 17 Mar 2017
5 night minimum stay
for 5 nights
Easter 2017
1 Apr 2017 - 28 Apr 2017
3 night minimum stay
for 3 nights
My Standard Rate
3 night minimum stay
for 3 nights

Additional pricing information

Refundable Damage Deposit £50
Pet Fee £25

Booking Notes:
Full payment is required within 6 weeks of booking; There is an additional £25 extra cleaning fee for pets per week; maximum 2 well behaved small dogs. Cheltenham Race Festival , Chrsitmas and New Year and all Bank Holiday weekends will attract a minimum night rate of not less than £85. There will be a security deposit of £50 per visit refundable within 7 days of departure provided there dis no discernible or irrevocable damage.Pet owners please note that we will decuct money if you allow dogs to soli bedding and towels.

Logs provided for the first open fire between 31st October and 31 March only.

Minimum 3 nights break; 2 night breaks considered but attract a higher pro rata rate

Please note that we do not accept payments on the day of arrival or after the accommodation has been occupied.

Also, cancellations made within 4 weeks of your arrival may not qualify for a full refund unless there are exceptional circumstances such as illness.

Changeover Day:
Friday to Friday, Friday to Monday, or Monday to Friday but can be flexible; please ask on booking.

Notes on prices:
The cottage costs from £55 per night for a minimum of 3 nights. Bank Holiday weekends, the Cheltenham and Paddy Power race weeks and Fri and Sat night only bookings between April and October will attract a higher pro rata or premium rate. Please request prices on application. Longer bookings can be as low as £50 per couple per night. Please ask on enquiry.

Owner's Cancellation Policy

100% refund for cancellations more than 30 days before check-in date.
Enter dates for accurate pricing
Total amount
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Updated: 05-Oct-2016
Available arrival


From the Owner

The cottage is in the heart of the town and it is possible to leave the car and walk to all amenities within 5 minutes. Recently refurbished, we offer superior comfortable accommodation while keeping the integrity of the country Bolt Hole. There is a lounge with 2 comfortable sofas, TV, DVD player and free WiFi. There is a large open fire (logs are available in season). The newly fitted deluxe bathroom has a bath big enough for two and towelling robes and slippers can be provided on request for that special occasion and some extra luxury. The dining room seats four and can accommodate an extra person if necessary. The patio garden with table and chairs can be accessed from the modern well-equipped kitchen and is spacious enough for breakfasts, aperitifs and meals outside in the summer. There is a shed for cycles and plenty of room for muddy boots.

Property Type

  • cottage


  • Away From It All
  • Historic
  • Romantic


  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine


  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Hob
  • Toaster


  • Dining ...
  • Dining Room


  • Books ...
  • DVD Player
  • Stereo ...
  • Television
  • Video Library ...


  • Long-term Renters Welcome
  • non smoking only ...
  • not suitable for children ...
  • pets considered ...
  • wheelchair inaccessible ...

Location Type

  • rural
  • town


  • arboretum
  • autumn foliage
  • churches
  • forests
  • library
  • restaurants

Leisure Activities

  • bird watching
  • horse riding
  • scenic drives
  • sight seeing
  • walking

Local Services & Businesses

  • ATM/bank
  • groceries
  • massage therapist

Sports & Adventure Activities

  • cycling
  • equestrian events
  • golf
  • hiking


  • Bathroom 1 - Toilet, Bath (no shower), Shower Enclosure, Spacious
  • One bathroom. Spacious with new white suite, includes large bath for 2 and a separate walk in shower


  • 1 Bedroom, Sleeps 2
  • Bedroom 1
  • Description of sleeping capacity: Sleeps 2 Notes on bedrooms: 1 king-size bed, goose down and/or hypo-allergenic duvets and all linen including luxury towels provided; wardrobe, 5 drawer chest of drawers, full length mirror in hall outside


  • Bicycles ...
  • Terrace ...
  • Golf ...
  • Garden ...
  • Barbecue ...
  • 1 bicycles


  • Self-catering


  • Notes on accommodation: The stairs to bedroom, bathroom and garden are very steep and are unsuitable for those with mobility issues or small children and/or those carrying babies, including heavily pregnant women. On street parking from 5.00 pm to 8.00 a.m. at no charge. Daytime parking in Back Lane car park (£1 per day). Car park is adjacent to library, 5 mins walk from cottage. The garden is enclosed and secure from the road. Outside: Patio with table and chairs; bike shed Steps up to large enclosed lawned area Utility Room: Cupboard for boots and coats Cleaning / Towels / Linen / Maid service: All linen including towels and tea towels provided; change once per week; Hairdryer and fan in bedroom Bathrobes and slippers provided at £5 per person per week; please request at time of booking Other: Dining room off kitchen, table seats four

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