Sample the Cotswolds on a circular self-guided walk between Bourton-on-the-Water and Winchcombe. Accommodation, bag transfer and custom holiday pack included.

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 £375 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
Cotswold Round
Cotswold Highlights Trail
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 £375 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.

Code	Tour	Duration	Difficulty	Price per person
COTSB	A circular trail beginning at Bourton-on-the-Water	3 nights, 2 days walking	Moderate	£375
COTSB-D	A circular trail beginning at Bourton-on-the-Water Dog friendly	3 nights, 2 days walking	Moderate	£375

Code	Tour	Duration	Difficulty	Price per person
COTSB	A circular trail beginning at Bourton-on-the-Water	3 nights, 2 days walking	Moderate	£375
COTSB-D	A circular trail beginning at Bourton-on-the-Water Dog friendly	3 nights, 2 days walking	Moderate	£375