This self-guided walking holiday captures the classic English Village lifestyle. Take in the beauty of the charming honey coloured Cotswold cottages and the dignified manor houses. Explore ancient wool churches and quintessential English countryside followed by relaxing in a traditional English Pub.

4 –10 NIGHTS Available Cheltenham, England

By Rail: Great Western Railway operate regular connections to London with approximately hourly Cheltenham Spa to Swindon services which extend to through to Didcot Parkway, Reading & London Paddington.

By Car: Cheltenham can be easily accessed via major UK roads and motorways. Cheltenham's direct approach is via Junction 11 of the M5, follow signs for the town centre.


Hotel Category

B&Bs, Hotels and Inns (3*) or Luxury Hotels (5*).

Luggage Transfer

The tour includes transfer of luggage as stated. The tour information pack provided to the clients 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

  • Moreton-in-Marsh

Daily Distance Range

  • Minimum:6 miles / 10 km per day
  • Maximum:12 miles / 19 km per day

Duration (Nights)

This tour has a variety of durations from 4 nights to 10 nights.


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 with colour coded routes on local maps
  • 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

The maximum altitude on this tour is approximately 984 feet.


Arrive in Cheltenham. Stay overnight. Cheltenham is England’s most complete Regency Town and is home to a thriving restaurant scene, boutique shopping and period architecture.

A: Circular route from Cheltenham via Leckhamptonand Seven Springs (Full route: 12 miles / 19km | Short Route: 8 miles / 13km)

Hike out of Cheltenham to the top of Leckhampton Hill, where you will be rewarded by some superb views of the Severn Vale and Cheltenham as well as some interesting historical sites. Continue on through the village of Coberley where you will then find the church of St. Giles. Its unexpected setting and grand monuments tells a long history of the village that now stands. The walk will also take you to Seven Springs, the disputed source of the River Thames.

Stay overnight in Cheltenham. No luggage transfer required.

B: Circular route from Cheltenham via Winchcombe (Full route: 10 miles / 16km | Short Route: 6 miles / 10km)

This walk starts with a short bus journey to the small ancient town of Winchcombe. Home to Sudeley Castle, it is a walk of stark contrasts, cross the open grassland of Cleeve Common to reach the highest point of the Cotswolds before 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. No luggage transfer required.

C: Circular route from Cheltenham via Cranham (Full route: 9.5 miles / 15km | No Short Route)

A bus journey takes you to the start of this walk. The first half follows tracks and paths through the extensive beech woods around Cranham and the second half takes you along the Cotswold escarpment with its stunning views over to Crickley Hill. The bus is payable locally and costs from £3 up to £5 per person.

Stay overnight in Cheltenham. No luggage transfer required.

D: Linear route from Cheltenham to Bourton-on-the-Water (Full route: 11 miles / 17 km | Short Route: 6.5 miles / 10 km)

Clients will be collected for a short transfer to Chedworth Roman Villa or Northleach (client preference) before walking to Bourton-on-the-Water. The beautiful pastures and woods along the banks of the little River Colnare the setting for the best exposed Roman villa in the country. The handsome little market town of Northleach provides an excellent introduction to this countryside. Its large 15th century wool church, built by the wealthy merchants, is typical of the Cotswold style while the Heritage Centre gives a fascinating insight into traditional farming life. The walk follows the Monarch's Way through unspoilt hamlets and over rolling country to Bourton in the valley of the River Windrush. This is the most famous village in the area with a wide range of attractions including museums, a perfumery and a delightful maze.

Stay overnight in Bourton-on-the-Water. Luggage will be transferred.

E: Circular route from Bourton-on-the-Water (Full route: 11 miles / 17 km | Short Route: 8 miles / 12 km)

A walk over rolling hills through mixed farmland takes you up to Cold Ashton. Here you can rest in a traditional English pub before strolling on to Naunton where pretty stone cottages nestle in a valley surrounded by sheep, pleasant countryside and horse racing gallops. Follow the River Windrush down through lush meadows and woods past a lost medieval village back to Bourton.

Stay overnight in Bourton-on-the-Water. No luggage transfer required. 

F: Linear route from Bourton-on-the-Water to Stow-on-the-Wold (Full route: 8 miles / 12 km | Short Route: 6.5 miles / 10 km)

Two beautiful riverside villages will feature on today’s walk. Lower and Upper Slaughter, on the banks of the little River Eye, are among the most popular in the Cotswolds. The charming cottages, manor houses and water mill which are being restored to full working order, are favourite subjects for local artists who regularly exhibit their work in the village hall. Lower and Upper Swell on the River Dickler are equally pleasant with cosy country inns and unique features like the Georgian therapeutic well. The town of Stow-on-the-Wold has a number of handsome stone buildings that stand around the ancient market square that once hosted some of the greatest sheep fairs in the country.

Stay overnight in Stow-on-the-Wold. Luggage will be transferred.

G: Circular route from Stow-on-the-Wold (Full route: 10.5 miles / 16 km | Short Route: 7.5 miles / 12 km)

Stroll out through secluded villages to join the Oxfordshire Way through the wide valley of the River Evenlode. The walk here combines wide views across to the Wychwood with visits to Icomb, Bledington and Oddington, often missed from the tourist trails. Enjoy the peace of the countryside as you stroll past delightful cottage gardens, medieval church wall paintings, village greens and charming manor houses on the way back to Stow on the Wold.

Stay overnight in Stow-on-the-Wold. No luggage transfer required

H: Linear route from Stow-on-the-Wold to Moreton-in-Marsh (Full route: 8 miles / 12 km | Short Route: 6.5 miles / 10 km)

Continue up the Evenlode Valley past the typically English manor at Donnington and the surprising Oriental house at Sezincote. Here the 18th century manor is built in the Indian style with water gardens.Moreton in Marsh stands either side of a broad main street lined with fine houses, shops and inns.

Stay overnight in Moreton-in-Marsh. Luggage will be transferred.

I: Circular route from Moreton-in-Marsh (Full route: 6.75 miles / 10 km | No Short Route)

The village of Blockley is one of the jewels of the Cotswolds that is often overlooked. The little stream that runs through it once supported a dozen mills that were used for all manner of industry from flour milling to silk weaving. The delightful old buildings, ponds and streams now offer wonderful opportunities for creative gardeners. At Batsford there is gardening on a much larger scale with an Arboretum inspired by the mountain sides of Asia Minor and a Cotswold Villages WalkingSept 2019 V001Falconry Centre running regular demonstrations. The cottages, church and 14th century tithe barn at Bourton on the Hill make a wonderful and very English scene.

Stay overnight in Moreton-in-Marsh. No luggage transfer required. ​



Routes D, F and H are mandatory and must be included on all tours starting from 4 nights, however all other routes can be combined as preferred by you / your client to create a tour between 5 and 10 nights. We recommend:

6 days, 5 nights: Routes D E F and H

7 days, 6 nights: Routes D E F G and H

8 days, 7 nights: Routes D E F G H and I

9 days, 8 nights: Routes A D E F G H and I

10 days, 9 nights: Routes A B D E F G H and I

11 days, 10 nights: Routes A B C D E F G H and I

Important Information


The correct clothes are important to ensure comfort during each walk. We suggest avoid anything 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