Exploring the Cotswolds - 8 days

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  • No booking fees
4.5 Based on 7 Reviews
  • Walking tour
  • Hiking
See Itinerary
  • duration 8 days
  • tour type Private
  • age requirement 18+ years old
  • max group size 20
  • guiding method Self guided/Independent
  • Starts Stratford-upon-Avon, England
  • Ends Winchcombe, England
  • +5
HIGHLIGHTS Download trip notes
  • Discovering the typically English countryside
  • Walking parts of the Cotswold Way
  • Enjoying the flexibility of walking with a daypack from village to village
  • Experiencing the hospitality in the warm family run B&B’s and guesthouses
Start in Stratford-upon-Avon and end in Winchcombe, the trip Exploring The Cotswolds - 8 Days is a self-guided walking trip that takes 8 days. You will travel through Broadway, Winchcombe, Guiting Power and 4 other destinations in England. Exploring The Cotswolds - 8 Days is a private trip which includes accommodation, transport, meals and others.

This holiday is intended to appeal to those who want a gentle introduction to walking in the English countryside; the Cotswold’s are hilly rather than mountainous - the highest point being little more than 1000 feet above sea level. Officially designated as an Area of Outstanding Natural Beauty, the Cotswold landscape is an entrancing mixture of parkland, cultivated fields with dry-stone walls of Jurassic limestone, and patches of unspoilt woodland. Stone-built, also, are almost all the cottages, farmhouses, villages, and small towns that our route passes. About half of our itinerary, around 50 miles (from Stratford-upon-Avon to Winchcombe), coincides with the Cotswold Way, a 102 mile Long Distance Path that is claimed to be the best waymarked in England.
4.5 - Excellent
Based on 7 reviews
  • Anonymous
  • On Oct 07 2019
4 - Very Good
Very Good
“Trina Willis did a good job answering questions, and helped us with handling of extra bag. The accomodations in general were good, with Three Ways House our favorite, as it had both a very nice room and great restaurant. Diane enjoyed the Pudding Club. The two not up to the same standards on rooms were the The Crown Inn in Blockley and the Wesley House. However, the restaurants were good with the Wesley House very good. In general we enjoyed the hikes. In the future we would be more interested in hikes where we had a base camp and could stay for 3 days, rather than moving each day, which required constantly repacking of our luggage.”
  • Anonymous
  • On Jun 11 2019
5 - Excellent
“We enjoyed a lovely week of walking in this beautiful part of England. We can't speak highly enough of the accommodation. The notes and maps provided were excellent.”
  • Anonymous
  • On Oct 30 2018
5 - Excellent
“We had the most fabulous time in every way possible. The weather was so sunny and warm that we never used our rain jackets that we brought along with us. The walking footpaths were perfect as were the maps that you sent for us to follow. Our accommodations were all wonderful - - our favorites were Mil-Mar in Stratford (sweetest couple running the B&B there), Three Ways Hotel in Mickleton, and Lansdowne in Burton-on-the-Water. The Sherpa service was absolutely perfect and we recommend them without reservation. What an absolutely delightful holiday. Thank you so very much for attending to all the details.”
  • Anonymous
  • On May 14 2018
5 - Excellent
“Too many high points to name - ancient old villages (day 5 had the most), beautiful views of countryside, sheep with newborn lambs everywhere, beautiful fields with hedges all around, all the fruit trees in color, woods with huge old trees, friendly people, pubs. There was a lot of mud due to heavy rainfall before we arrived, it made the steep descent on day 2 very difficult. Strongly recommend 100% waterproof boots, rain pants, walking sticks and know how to read a compass before travelling.”
  • Day 1 : Arrive Stratford-upon-Avon
  • Day 2 : Walk to Mickleton via Hidcote Gardens - 17 km/10.5 miles, 5.5 h
  • Day 3 : Walk to Broadway via Chipping Campden Fish Hill - 14.5 km/9 miles, 4 h
  • Day 4 : Walk to Blockley - 19.3 km/12 miles, 6 h
  • Day 5 : Via Batsford and Lower Slaughter to Bourton on the Water - 21.5 km/13 miles, 7 h
  • Day 6 : Walk to the tiny gem village of Guiting Power - 11.6 km/7 miles, 4 h
  • Day 7 : Walk via Hailes Abbey & Sudeley Castle to Winchcombe 18.5 km/11.5 miles, 6 h
  • Day 8 : Arrangements end after breakfast
  • 7 nights B&B accommodation on a twin share basis usually with ensuite facilities
  • Information pack including route notes & maps (1 pack per room booked)
  • 6 breakfasts
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 20kg
  • Emergency hotline
  • Travel to Stratford and from Winchcombe
  • Lunches, dinners and drinks
  • Transfers
  • Items of a personal nature
  • Travel insurance
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GOOD TO KNOW Download trip notes

No additional cancellation fees apply for this Exploring the Cotswolds - 8 days tour. You can cancel the tour up to 70 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 69 days of departure.


For any tour departures within 09 October 2021, full payment is required. For tours that depart later than 09 October 2021, a deposit is required to confirm this tour, and the remaining balance will be charged 69 days before trip departure.

Travel Insurance

Exploring the Cotswolds - 8 days tour requires that you have adequate and valid travel insurance covering medical and personal accidents, including repatriation costs and emergency evacuation. We recommend using World Nomads' travel insurance.


For this Exploring the Cotswolds - 8 days tour getting the required visa(s) is the responsibility for each individual traveller, as visa requirements vary depending on your nationality. We recommend to check with your local embassies representing the countries that you are travelling to, as part of this itinerary.

For Solo Travelers

A twin share room may not always be available for solo travelers as it depends on the final number of people on the tour. If you have picked twin share room while booking, and that option is not available, we will get back to you after booking. A single room might then be available against an additional fee.

If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us. We're ready to help.
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