Cotswold Short Break

Cotswold Short Break

A lovely two-day walk from Bourton-on-the-Water via Winchcombe and the Windrush Valley.

3 nights
27 miles

From £325 per person

Discover the available tours

About this route

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.

© Contours Walking Holidays Cotswold Short Break map
Circular trail beginning at Bourton-on-the-Water
27 miles (43 km)
19th March to 30th October

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.

Available tours

CodeTourDurationDifficultyPrice per person
COTSB A circular trail beginning at Bourton-on-the-Water 3 nights, 2 days walking Moderate£325

Cotswold Short Break 3 nights, 2 days walking

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

Travel to Bourton-on-the-Water where your first night's accommodation has been 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)


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; should your accommodation be further than this, transfers will be provided as standard.

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
£55.00 per person / per night
Single Supplement
£45.00 per person / per night

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

Extra night (Standard)
£60.00 per person / per night

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)
£60.00 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: 19th March - 30th October
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 actually involves two buses, 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.

Routes on this trail

Cotswold Highlights Trail
4 to 7 nights
45 miles
Easy to Demanding
Dog friendly
From £430 per person
A fantastic walk from Chipping Campden through the quintessentially English countryside of the Cotswolds.Find Out More
Cotswold Round
5 to 9 nights
49 miles
Easy to Moderate
Dog friendly
From £535 per person
A walk from Moreton-in-Marsh visiting the finest towns, villages and countryside in the Cotswolds.Find Out More
Cotswold Villages Trail
7 nights
60 miles
From £750 per person
A walking holiday from Moreton-in-Marsh through the many iconic settlements of the Cotswolds.Find Out More
"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)