Circular Walks in the Cotswolds

Circular Walks in the Cotswolds

A selection of circular walks through the beautiful countryside of the Cotswolds.

3 to 9 nights
27-60 miles
Easy to Demanding / Strenuous

From £365 per person

Find your holiday

About the trail

Strewn with countless pretty villages built by medieval merchants, the Cotswolds fulfils most people's idea of an idyllic English landscape. While walking in the Cotswolds, you will find neat fields, rolling green hills, ancient woodland and clear streams, combined with simple stone cottages and historical landmarks to create a truly unique picture of timeless beauty. Our selection of circular trails explores the scenery, settlements and stories that make the Cotswolds such a wonderfully special place to discover on foot.

Looking for the full Cotswold Way National Trail? Click here.

Choose your route

  • Cotswold Villages Trail
  • This route includes dog friendly tour options Cotswold Round
  • This route includes dog friendly tour options Cotswold Highlights Trail
  • This route includes dog friendly tour options Cotswold Short Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

About this route

3 nights
27 miles
Moderate
2nd January to 24th December
Includes Dog-Friendly Tours

From £365 per person

Cotswold Short Break

This scenic short tour combines two contrasting trails linking Bourton-on-the-Water with Winchcombe to provide a delightful two-day walk through some of the loveliest countryside in the Cotswolds.

Starting at Bourton-on-the-Water, the route follows the Warden’s Way through the idyllic villages of Lower and Upper Slaughter, Naunton and Guiting Power before descending to Winchcombe past Sudeley Castle.

On the second day, the route follows the Windrush Way over the hills past several lost medieval villages before following the River Windrush back to Bourton-on-the-Water. This short walking route is packed with gorgeous scenery and historic sites throughout, making this an ideal mini getaway.

Available tours

Code Tour Duration Difficulty Price per person
COTSB A circular trail beginning at Bourton-on-the-Water 3 nights, 2 days walking Moderate £365

Short breaks

Code Tour Duration Difficulty Price per person
COTSB A circular trail beginning at Bourton-on-the-Water 3 nights, 2 days walking Moderate £365

Cotswold Short Break 3 nights, 2 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather
  • Holiday Highlights
Start

Travel to Bourton-on-the-Water where your first night's accommodation will be booked

Day 1

Bourton-on-the-Water to Winchcombe. 13.5 miles (21.5km)

Day 2

Winchcombe to Bourton-on-the-Water. 13.5 miles (21.5km)

Finish

Depart from Bourton-on-the-Water after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£65.00 per person / per night
Single Supplement
£55.00 per person / per night


You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Bourton-on-the-Water)
£80.00 per person / per night
Standard
Interactive
© Contours Walking Holidays Cotswold Short Break map
Circular trail beginning at Bourton-on-the-Water
27 miles (43 km)
2nd January to 24th December

Holiday highlights

Passing the impressive Sudeley Castle near Winchcombe, once the home of Queen Katherine Parr.

Experiencing the varying scenery as you follow the Warden’s Way and pass through the lush Windrush Valley.

Discovering plenty of historic surroundings, including the remains of a Norman Castle in Upper Slaughter and the ‘lost’ medieval villages on route to Bourton-on-the-Water.

What's included?

  • 3 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

Winchcombe is a popular choice for a rest day. It is a charming small town with two or three inns, many attractive old Tudor houses, cottages with roses clambering over their porches and a fine church containing an altar cloth worked by Catherine of Aragon, Henry VIII's first wife. Forty-five grotesque gargoyles, each representing a local character from the 1460s, adorn its outer walls. Winchcombe is also a good base for exploring Sudeley Castle and its romantic gardens.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Bourton-on-the-Water)
£80.00 per person / per night

Tour Facts

Total distance: 27 miles (43 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 13.5 miles (21.5 km)
Maximum daily distance: 13.5 miles (21.5 km)
Code: COTSB Grade: Moderate
Season: 2nd January - 24th December
Start of holiday: Bourton-on-the-Water
End of holiday: Bourton-on-the-Water

Route Profile

Cotswold Short Break Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Bristol and Birmingham.

By Rail - The nearest rail stations to Bourton-on-the-Water are either Moreton-in-Marsh (about 8.5 miles away) or Cheltenham Spa (about 16.5 miles away).

By Bus - Buses run from/to both Moreton-in-Marsh & Cheltenham to Bourton-on-the-Water Monday to Saturday only, so a taxi will be required on a Sunday (the journey from/to Cheltenham in particular is rather lengthy, so a taxi is probably a more convenient option on any day).

From London - Trains run from London Paddington station to Moreton-in-Marsh.

Return To The Start - The Cotswold Short Break is a circular tour beginning and ending in Bourton-on-the Water.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.
"Sudeley Castle" by Helen and Liz Boyd (2022) "Sudeley Castle" by Helen and Liz Boyd (2022)
"Hedgehog on the Trail" by Helen and Liz Boyd (2022) "Hedgehog on the Trail" by Helen and Liz Boyd (2022)
"Old Mill at Lower Slaughter" by Elizabeth Bradley (2017) "Old Mill at Lower Slaughter" by Elizabeth Bradley (2017)
"Wardens Way" by Elizabeth Bradley (2017) "Wardens Way" by Elizabeth Bradley (2017)
"Windrush Way" by Elizabeth Bradley (2017) "Windrush Way" by Elizabeth Bradley (2017)
"Wardens Way Sheep" by Elizabeth Bradley (2017) "Wardens Way Sheep" by Elizabeth Bradley (2017)