The Cotswold Way is one of the UK’s managed National Trail footpaths, running 103 miles from the market town of Chipping Campden in the North of The Cotswolds, to the spa town of Bath in the South. The route crosses typical Cotswold countryside with a patchwork of fields partioned by traditional honey coloured dry stone walls across rolling hillside. This short break is based in Cheltenham and allows you to discover part of the 102 mile route, along with historic buildings and glorious gardens. 

2 - 4 NIGHTS Available Cheltenham, England

By Rail: The nearest railway station is Cheltenham Spa, which is easily reached from London by train. There will be a short walk or taxi ride to your overnight accommodation,which we are happy to arrange on guests’ behalf. 

By Car: Cheltenham is easily accessible via the M4/M5 route or by the A40 from London via Oxford. 


Hotel Category

B&Bs, Hotels and Inns (3*) or Luxury Hotels (5*). Please note the Luxury version includes some taxi transfers at the beginning or end of some days.

Luggage Transfer

The tour includes transfer of luggage as stated. The tour information pack contains luggage tags from Compass Holidays. The clients name and the hotels used throughout the holiday will be on these tags. They should be fixed to the luggage. In the morning the luggage should be left at the reception for collection. Luggage is collected after 9.30am and delivered to the next hotel before 4.30pm.

Grade (Difficulty)

This grade of this tour is moderate.

Start Location

  • Cheltenham

End Location

  • Cheltenham

Daily Distance Range

  • Minimum: 6 miles / 10 km per day
  • Maximum:7 miles / 11 km per day

Duration (Nights)

This tour runs for 2-4 nights but can be extended or decreased by changing the daily distance.


This tour is available from January until December


What we'll give. What we won't

What is included in the tour

  • Accommodation at the stated category with breakfast
  • Luggage Transfers
  • Full Tour Pack
  • Smartphone App with GPS routes
  • 24-hr emergency helpline

What is NOT included in the tour

  • Lunch, Dinner & Drinks
  • Entrance to attractions
  • Buses and/or Ferries unless otherwise stated
  • Tourist Taxes where applicable

Arrive Cheltenham and stay overnight. 

Cheltenham is the most complete Regency town in the UK with extensive period architecture, a fantastic foodie scene, and museums attributed to Cheltenham’s famous sons – Gustav Holst composer of The Planets and Edward Wilson, polar explorer, naturalist, physician, and artist.   


A: Winchcombe to Cleeve Hill( 6 miles / 10 km)  

The day begins with a steam train ride on the Gloucestershire Warwickshire Railway from Cheltenham Racecourse to Winchcombe.  On days when the trains aren’t running, we can arrange transportation to a drop off point. Trains run from Easter to September, every day except Monday and Friday.  (COVID dependent) 

A highlight of Winchcombe is Sudeley Castle & Gardens, surrounded y the rolling hills of the Cotswolds National Landscape, and the final resting place of Catherine Parr, Henry VIII’s final wife. 

To start the walk, leave through the Sudeley Estate, climbing steadily to the ancient Neolithic long barrow of Belas Knap to Cleeve Hill – the highest point in The Cotswolds – then descending into Prestbury. Prestbury is supposedly the most haunted village in England. After this you will head back to the elegant town of Cheltenham Spa. 

Stay overnight in Cheltenham.  


B: Cheltenham 

Explore the delightful regency town of Cheltenham, taking in the most interesting examples of Regency architecture as well as exploring the town's history, and the stories of some of the famous people who have lived in the town. 

Cheltenham has a growing number of respected independent restaurants - offering everything from French cuisine to award-winning fish and chips, to Sri Lankan street food. There is also a wide selection of well-known branded food outlets, family favourites, and new restaurants with various awards to their name. Harden’s, The Good Food Guide, The Michelin Guide, and The Good Pub Guide all lavish praise on innumerable Cheltenham restaurants.  

Experiences include the Regency Cycle Trail (a 6-mile bike ride around the town), and food and drink tours to venues such as Dunkerton’s Cider Sibling Distillery and Battledown Brewery. Cheltenham is renowned for its beautifully landscaped public parks and gardens. 

Stay overnight in Cheltenham.  


C: Cleeve Hill to Leckhampton ( 6 miles / 10 km) 

Returning to the viewpoint of Cleeve Hill from your overnight accommodation, proceed across Cleeve Common which affords extensive views to Gloucester and the distant Malvern Hills, before you continue onto Charlton Kings Common with its breath-taking views across Cheltenham and the Severn Vale. Follow the escarpment past Seven Springs and on to Leckhampton Hill where you can spot the distinctive rock pillar known as the Devil’s Chimney.  

Stay overnight in Cheltenham. 


D: Birdlip to Painswick (7 miles / 11 km)  

From Birdlip, the trail passes the remains of Great Witcombe Roman Villa, through magnificent beech woodlands and on to Coopers Hill, the site of the crazy annual cheese-rolling event every May which sees competitors chase a cheese wheel down the very steep slope. The route then emerges onto the common land of Painswick Beacon, where the ramparts of an Iron Age hill fort can clearly be seen. The section ends in the picturesque town of Painswick, the mid-point of the Cotswold Way. Painswick featured in J.K.Rowling’s novel dramatisation “A Casual Vacancy” and is also home to the Rococo Gardens which are worth a visit. There is a historic legend regarding the 99 yew trees in St Mary’s Churchyard.  Apparently, the Devil refused to let the 100th one grow! 


The routing will be as follows using the Route letters above:

The 5 day, 4 night holiday will be routed A B & C

The 4 day, 3 night holiday will be routed around 2 routes of your choice of A, B or C 

The 3 day, 2 night holiday will be routed around 1 route of your choice of A, B or C 

Important Information


The correct clothes are important to ensure comfort during each walk. We suggest avoidanything with seams and buttons in sensitive areas. Clothing should take moisture from the body to the outside. Sweatshirts, thin pullovers and breathable jackets are ideal companions during the cooler days. Take light, waterproof jackets and trousers in case there is rain. On hot days we suggest a cap or hat and sunglasses to protect from the sun.

Pickup point
Cheltenham, UK View on Map