Explore the timeless Cotswolds on a circular walking holiday, accomodation and luggage transfer included. Visit honey-coloured villages and ancient woodland.

Circular Walks in the Cotswolds

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

3 to 13 nights

27-80 miles

Easy to Strenuous

From £280 per person

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.

Dog friendly tours available

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

Routes on this trail

Cotswold Highlights Trail

4 to 7 nights

43 miles

Easy to Demanding

Dog friendly

From £375 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

48 miles

Easy to Moderate

Dog friendly

From £460 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

Moderate

From £645 per person

A walking holiday from Moreton-in-Marsh through the many iconic settlements of the Cotswolds.Find Out More

South Cotswold Walk

7 to 13 nights

80 miles

Easy / Moderate+

From £645 per person

A pleasant walk from Winchcombe through the tranquil countryside of the southern Cotswolds.Find Out More

Winchcombe Way

3 to 5 nights

43 miles

Moderate+

Dog friendly

From £280 per person

An double-loop route showcasing the northern Cotswolds with Winchcombe at its centre.Find Out More

Cotswold Short Break

3 nights

27 miles

Moderate

Dog friendly

From £280 per person

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

Customer reviews from the Circular Walks in the Cotswolds

“Accommodations were charming, the walk was exactly what we expected, and the folks at Contours who helped us with all our requirements and changes were unfailingly courteous and prompt.”
Mr Zimmerman, USA

“The Cotswolds are beautiful and being able to walk during the day and have my bags taken to my next night's accommodation was fabulous.”
Ms Birnie, Australia

“3rd Contours holiday so we must enjoy them - we keep coming back. When we booked on a week that had a special event, you were able to find us a different route”
Dr Rudolph, USA