Views on a walking holiday in the Cotswolds, peering over a drystone wall to lush green fields hemmed with hedgerows and deciduous trees.

Walking Holidays in the Cotswolds

Escape into gentle countryside on a walking holiday in the Cotswolds. This well-loved part of the country is perfectly set up for walkers, full of winding pathways through wooded and pastoral landscapes between beautiful stone-built towns full of independent shops, eateries and inns.

We offer a range of short breaks and full-length tours across the Cotswolds, with flexible itineraries to accommodate your walking pace – and the urge to stop and indulge at every pub or teashop along the way. Tour those Cotswold towns and local estates on our circular short breaks, or choose the Cotswold Way to experience the region’s wilder side, with steep climbs to sweeping views from the Cotswold escarpment.

Find Your Holiday:

Circular WalksFewer MovesThe Cotswolds' National TrailPassing Through the CotswoldsBring Your Dog

Circular Walks in the Cotswolds

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Return to where you started to fully appreciate the area — and for easy onward travel.

Discover the Trails

Art in the Contours Holidays colours of a traditional market hall built in Cotswold stone, found on the Cotswold Highlights Walking Holiday.

Cotswold Highlights Trail

  • 4–7 nights
  • 45 miles
  • Easy–Demanding

Tour Stow-on-the-Wold, Winchcombe, Stanton and Broadway on this showpiece trail through the most famous towns and villages of the Cotswolds. The Cotswold Highlights Trail combines a ramble through the heart of the Cotswolds with sections through its western fringes, where you'll explore deciduous woodland, crowned by the trees at Batsford Arboretum, and well-kept fields.

Art in the Contours Holidays colours of Broadway Tower, a striking stone-built landmark on the Cotswold Round walking holiday.

Cotswold Round

  • 5–9 nights
  • 49 miles
  • Easy–Moderate

Combine the northern edge of the Cotswolds Highlights Trail through Chipping Campden and Moreton-in-Marsh with a more widely sweeping southern arc that includes Naunton and the famous Slaughters. The Cotswold Round includes a particularly scenic leg through Windrush Valley, incorporating lakes and natural reserves.

Art in the Contours Holidays colours of a swan, a common sight on the Cotswold Short Break.

Cotswold Short Break

  • 3 nights
  • 27 miles
  • Moderate

Tour there and back again between Bourton-on-the-Water and Winchcombe on two distinct trails: the Warden's Way and the Windrush Way. You'll delve into Lower and Upper Slaughter, Nauton and Guiting Power along the way, all beautiful Cotswold villages that deliver that chocolate-box charm.

Art in the Contours Holidays colours of a pretty Cotswold village.

Cotswold Villages Trail

  • 5–9 nights
  • 49 miles
  • Easy–Moderate

Visit twenty-seven Cotswold villages on this complete tour of the area, including hikes out to historic hill forts, a gothic folly, a medieval abbey and the beautiful Sudeley Castle. Some of our favourite sights include the old wool market town of Stow-on-the-Wold, the medieval cottages of Northleach, and Chipping Campden's beautiful limestone buildings, market square and church.

Fewer Overnight Accommodations

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Settle in to see more of each Cotswold village with multiple nights in the same place.

Discover the Trails

Art in the Contours Holidays colours of the structure of a twin-centre walking holiday, with circular day walks from the first accommodation, a crossover walk to the next accommodation, and several circular day walks from this new base.

Cotswold Twin Centre

  • 6 nights
  • 64 miles
  • Moderate

Devised by Contours Holidays, the Cotswold Twin-Centre route twines through the Cotswolds from two overnight bases: Tetbury and Cirencester. The trail offers manicured walking through the National Arboretum and Cirencester Park, with famous estates like Chavenage and Highgrove en route, alongside broadleaved woodland and canalside stints between stunning market towns with plenty to see and do.

Art in the Contours Holidays colours of the structure of a two-night break, with a single central accommodation, a lift to the start of the trail and a lift on the second day back to your accommodation.

Stow-on-the-Wold Two-Night Break

  • 2 nights
  • 12–27 miles
  • Easy to Demanding

From your base at the highest town in the Cotswolds, Stow-on-the-Wold, you'll hike through forests, farmland and market towns on your first day's walk. On the second, enjoy leafy lanes and riverside paths. We offer three different lengths of our two-night breaks, so you can choose the daily distances that suit your pace.

The Cotswolds' National Trail

The UK's National Trails are impactful, well-waymarked walks, crossing historic countryside with a strong story behind each route. In the Cotswolds, expect lofty views over beautiful countryside full of stunning architecture.

Discover the Trails

Art in the Contours Holidays colours of a common buzzard, a large bird of prey often seen wheeling over the Cotswold escarpment on the Cotswold Way.

Cotswold Way

  • 4–16 nights
  • 26–102 miles
  • Easy/Moderate–Demanding/Strenuous

Home to unmatched views over the Cotswolds Area of Outstanding Natural Beauty, the Cotswold Way hikes high over the western edge of the Cotswolds. History is rife along this route, in ancient commons, stately homes, market towns and historic battlesites. Local towns are sure to make an impression, too, including Broadway, Winchcombe, Painswick and the stunning Roman city of Bath.

Passing Through the Cotswolds

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Contrast the stone architecture and pastoral scenes of the Cotswolds with the rolling expanse of the Wessex Downs.

Discover the Trails

Art in the Contours Holidays colours of a stone bridge built over the Kennet and Avon Canal Path.

Kennet and Avon Canal

  • 4–7 nights
  • 45 miles
  • Easy–Demanding

At its western end, the Kennet and Avon Canal Walk takes in green views over the river in the southernmost region of the Cotswolds. Most striking is the city of Bath, all golden stone and historic features like the eponymous Roman baths, old pump room, the Georgian Crescent and Pulteney Bridge, and the Jane Austen Museum. Our stile-free holiday skips the eastern half of the walk to dwell primarily in the Cotswolds at the trail's western end.

Art in the Contours Holidays colours of three dogs - a beagle, a terrier and a sighthound - walking from right to left across the page.

Dog-Friendly Walking Holidays in the Cotswolds

With its long rural trails and plenty of independent eateries ready to welcome furry friends, the Cotswolds is the ideal place for a dog-friendly walking holiday. Hike through woodland trails and along glittering riversides, then lounge outside honey-stone pubs with your pooch as the sun winds down.

Your dog will benefit from their own luggage allowance and pleasant overnight stays at your accommodation with you. Read more about how dog-friendly walking holidays work, or go ahead and choose from the following tours:

More Holidays By Location

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Looking to explore another part of the UK? Here are a few of our most popular locations, with a host of trails to walk in each.  You're sure to find the right walk for you.

Art in the Contours Holidays colours of two dolphins swimming off the coast of Cornwall.

Cornwall

Art in the Contours Holidays colours of a market building in the Cotswolds.

Cotswolds

Art in the Contours Holidays style of a packhorse bridge in the Lake District.

Lake District

Art in the Contours Holidays colours of an old factory building in the Peak District.

Peak District

Art in the Contours Holidays colours of the Wolds Way stone-carved seat, found on the Yorkshire Wolds Way and Cleveland Way in Yorkshire.

Yorkshire