This walk through the Cotswolds starts in the historic Regency spa town of Cheltenham and explores the quintessentially British villages of the area. The Cotswolds are England's second largest Area of Outstanding Natural Beauty (the Lake District is first!) and with a combination of panoramic rolling hills, sites of historical interest and the archetypal golden-hued vilages, there is so much to explore! Enjoy the delights of Cheltenham before taking in some world-famous villages along the route, including Broadway, Bourton-on-the-Water and the Saxon capital of Winchcombe. There's even the option to take a side trip to visit Stratford-upon-Avon if a visit to Shakespeare's birthplace is calling you!
Your route takes you over Cleeve Hill, the highest point of the Cotswolds, to Sudeley Castle, the last resting place of Katherine Parr (Henry VIII's 6th wife). Visit some of the 'wool churches' of the Cotswolds - so named because of the input of finances from local, wealthy wool merchants back in medieval times to create elaborate and architecturally stunning buildings. Two of note on this route are in Winchcombe and Chipping Campden. Other points of interest along the route include some beautiful formal gardens at Kiftsgate or the Hidcote National Trust gardens. The River Windrush (after which the post-war West Indian immigration boat was named) forms part of the route back to Cheltenham from Bourton-on-the-Water.
Accommodation along the route has been hand-picked in Bed & Breakfasts with character, ranging from inns and townhouses to an old bakery. Offering a warm and friendly Cotswold welcome, as well as hearty breakfasts, they offer comfortable stops along the walk and a charming insight into Cotswold life.
On arrival in the historic spa town of Cheltenham you may well be tempted to explore the local area and some of its 'treasures' before finding somewhere to eat near the hotel.
Stay overnight at The Cheltenham Townhouse or similar
Starting from the classical Pump Room, the route crosses Cleeve Hill - the highest point of the Cotswolds - to Belas Knap long barrow and descends to Sudeley Castle and the ancient Saxon capital of Winchcombe, with its fine 'wool church'.
Breakfast included
Stay overnight at The White Hart Inn or similar
Follow the pilgrims' route to Hailes Abbey, then over the hills to Jacobean Stanway House and on to idyllic Stanton, before reaching the old coaching village of Broadway for your overnight.
Breakfast included
Stay overnight at the Hadley House Bed & Breakfast or similar
A half day's walking over the hills via Broadway Tower with its magnificent views to Chipping Campden. In the afternoon, explore this charming town with its silversmiths and 'wool church', or visit Dover's Hill, site of the annual 'Cotswold Olympiks', or the beautiful gardens at Kiftsgate or the National Trust gardens at Hidcote; or spend the afternoon at nearby Stratford-on-Avon, birthplace of William Shakespeare.
Breakfast included
Stay overnight at The Old Bakehouse B&B or similar
Pass through the charming villages of Broad Campden and Blockley and descend to Batsford, where you may visit the arboretum and falconry centre. On certain days of the week both Bourton House gardens and Sezincote House will be open. Finally, a pleasant stroll across meadows to the idyllic market town of Moreton-in-Marsh for your overnight stay.
Breakfast included
Stay overnight at The White Hart Royal Hotel or similar
After crossing the high wolds to Stow-on-the-Wold, complete with village stocks and picturesque square, the Cotswold Ring then passes through Lower Slaughter to Bourton-on-the-Water, prettily located on the River Windrush, with its many attractions.
Breakfast included
Stay overnight at The Lansdowne Guest House or similar
The Ring follows the pretty River Windrush through the delightful villages of Naunton and Guiting Power. Finally, a dramatic descent from the high wolds, through the meadows of the Cotswold escarpment, to journey's end in Cheltenham.
Breakfast included
Stay overnight at The Cheltenham Townhouse or similar
Breakfast included
During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.
To find out more call our sales team on 01606 720199, use our live webchat (we're open until 5pm today) or email sales@headwater.com
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Set in Winchcombe, just over half a mile from Sudeley Castle, The White Hart Inn offers accommodation with a restaurant, free private parking, a bar and a garden. Among the facilities at this property are a 24-hour front desk and luggage storage space, along with free WiFi throughout. The inn features eight ensuite bedrooms (Classic or Superior) as well as a family room made up of three 'rambler' rooms with shared facilities. All guest rooms come with a flat screen TV and tea & coffee making facilities. Full English Breakfast is included daily.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Read customer reviews on Tripadvisor.
NEARBY:
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
Set in a 17th-century former coaching inn, the White Hart Royal Hotel is located in Moreton-in-Marsh’s historic town centre and boasts regal connections as King Charles I took shelter here during the English Civil War. A four-poster bed, private garden, spacious wet room and a roll-top bath feature in some of the individually designed bedrooms. Flagstone floors and an original inglenook fireplace are in the traditional Snug Bar and guests can also make use of the hotel’s two period lounges. Fresh, local ingredients are served on the traditional British menu in the Courtyard Restaurant.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Our aim is to provide holidays that are unbeatable for choice and flexibility. We've listed our most popular travel options below, however you aren't limited to these - we can tailor-make virtually any holiday to suit.
To find out more about the travel options available call our sales team on 01606 720199, use our live webchat (we're open until 5pm today) or email sales@headwater.com
This holiday does not include any flights or rail
Alternative transfers
If you require alternative transfers (because you will be arriving at a different time to our standard flights), then we can usually arrange these for you (there may be an additional charge).
Should you require overnight airport accommodation, airport parking or even a uniformed chauffeur to take your car from your departure terminal and park it for you, we can arrange this for you through Holiday Extras. You can book airport parking, airport hotels and executive lounges directly through their website - or call us on 01606 720199 for further details of all the services on offer. Early booking is recommended to obtain the best availability and prices.
Here at Headwater we thrive on feedback from our customers. It's the only way we can continue to develop, and where necessary improve, our services and ensure our holidays continue to be the best they can be. However, as this is a relatively new holiday, we don't yet have any customer reviews available.
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.
Find out about The Headwater Price Promise to ensure you're getting the very best value for money.
This 7 night self-guided walking holiday includes:
Hotel-to-hotel accommodation in a mix of , , and hotels
Breakfast daily
Management by your local Headwater-appointed agent
Route directions and maps
Luggage transfers between hotels
Route directions and maps
How to book:
For further details, or to check availability, speak to our sales team on 01606 720199 (we're open until 5pm today) or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).
Complete our holiday enquiry form - we'll get in touch when it's most convenient for you
Speak to our sales team on 01606 720199 - we're open until 5pm today
Use our live chat to ask us a question
| Departing | Tour only | Prices  |
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| 9th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 12th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 13th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 16th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 19th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 20th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 23rd Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 26th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 27th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| 30th Aug 2020 | £985 | Tour only: £985 | Check availability |
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| Departing | Tour only | Prices |
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| 2nd Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 3rd Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 6th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 9th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 10th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 13th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 16th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 17th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 20th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 23rd Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 24th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 27th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| 30th Sep 2020 | £1039 | Tour only: £1039 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 1st Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 4th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 7th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 8th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 11th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 14th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 15th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 18th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 21st Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 22nd Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 25th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 28th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| 29th Oct 2020 | £1019 | Tour only: £1019 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 1st Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 4th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 5th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 8th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 11th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 12th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 15th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 18th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 19th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 22nd Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 25th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 26th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| 29th Nov 2020 | £1019 | Tour only: £1019 | Check availability |
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| Departing | Tour only | Prices |
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| 3rd Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 4th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 7th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 10th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 11th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 14th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 17th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 18th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 21st Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 24th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 25th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 28th Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 31st Mar 2021 | £1019 | Tour only: £1019 | Check availability |
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| 1st Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 4th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 7th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 8th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 11th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 14th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 15th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 18th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 21st Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 22nd Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 25th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 28th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| 29th Apr 2021 | £1019 | Tour only: £1019 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 2nd May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 5th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 6th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 9th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 12th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 13th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 16th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 19th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 20th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 23rd May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 26th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 27th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| 30th May 2021 | £1039 | Tour only: £1039 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 2nd Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 3rd Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 6th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 9th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 10th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 13th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 16th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 17th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 20th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 23rd Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 24th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 27th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| 30th Jun 2021 | £1039 | Tour only: £1039 | Check availability |
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| Departing | Tour only | Prices |
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| 1st Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 4th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 7th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 8th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 11th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 14th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 15th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 18th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 21st Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 22nd Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 25th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 28th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| 29th Jul 2021 | £1059 | Tour only: £1059 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 1st Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 4th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 5th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 8th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 11th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 12th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 15th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 18th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 19th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 22nd Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 25th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 26th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| 29th Aug 2021 | £1059 | Tour only: £1059 | Check availability |
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| Departing | Tour only | Prices |
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|---|---|---|---|
| 1st Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 2nd Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 5th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 8th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 9th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 12th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 15th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 16th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 19th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 22nd Sep 2021 | £1039 | Tour only: £1039 | Check availability |
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| 23rd Sep 2021 | £1039 | Tour only: £1039 | Check availability |
| Check availability | |||
| 26th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
| Check availability | |||
| 29th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
| Check availability | |||
| 30th Sep 2021 | £1039 | Tour only: £1039 | Check availability |
| Check availability | |||
| Departing | Tour only | Prices |
|
|---|---|---|---|
| 3rd Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 6th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 7th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 10th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 13th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 14th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 17th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 20th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 21st Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 24th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 27th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 28th Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 31st Oct 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| Departing | Tour only | Prices |
|
|---|---|---|---|
| 3rd Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 4th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 7th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 10th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 11th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 14th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 17th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 18th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 21st Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 24th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 25th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
| 28th Nov 2021 | £1019 | Tour only: £1019 | Check availability |
| Check availability | |||
The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.
Children
Please contact us for child prices.
Holiday type
Self-guided walking Managed locally by Headwater appointed agent.
Departures
Daily from 9th Aug 2020 to 28th Nov 2021, for 7 nights. All dates are subject to availability, please contact us to check.
Meals
Breakfast daily
This holiday does not include any flights or rail.
For further details, or to check availability, speak to our sales team on 01606 720199 (we're open until 5pm today) or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).
Complete our holiday enquiry form - we'll get in touch when it's most convenient for you
Speak to our sales team on 01606 720199 - we're open until 5pm today
Use our live chat to ask us a question
Please note: The prices and travel options shown are provided for customers based in, and travelling from/to, the UK. We are happy to arrange holidays for non-UK customers however, if you are travelling from USA, Canada, Australia or New Zealand, we recommend that you contact your local agent as they can provide appropriate transport options and advice.
Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Walking the Cotswold Ring. Simply complete the form below (fields marked * are mandatory) and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.
Alternatively, you can call our sales team on 01606 720199 to discuss your requirements in more detail (we're open until 5pm today) or contact us via live chat for help and advice.
