The Cotswold Round

7 Days & 6 Nights 4.5 Read 28 reviews
  • Strolling through the Regency splendour of the Pittville Pump Room
  • Exploring the quiet lanes of picturesque Cotswold villages
  • Hand picked accommodation offering the warmest of welcomes
  • Discovering the numerous abbeys, historic houses and ruins which litter the area
  • Enjoying the friendly atmosphere and great food of a Cotswold country pub
Starting in the Regency town of Cheltenham this circular walk links the picturesque towns of the North Cotswolds with some of the most scenic walking in England. Walk between the most beautiful villages in the Cotswolds and discover why the Cotswolds are a honey pot for walkers. Typical Cotswold cottages and villages, lush green countryside, historic houses, welcoming country pubs and inviting shops make the Cotswolds a walkers paradise and during the week you spend in the Cotswolds you are sure to fall in love with the Cotswolds over and over again.
If your idea of heaven is beautiful green countryside, picturesque villages, delicious local food and charming B&B’s then you will adore walking in the Cotswolds. With the added treat of Cheltenham, this is my favourite week of walking in the Cotswolds.

Tour Type:

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years

Activity Level & Terrain

This trip is graded moderate. The trail follows well maintained footpaths, bridleways, open fields and some minor roads. It does involve some relatively steep ascent and descent from the escarpment and days of up to 14 miles walking. The longer days can be shortened by taking local buses or taxis.


The Cotswolds Round is not waymarked so you will need to be comfortable reading a map and know how to use a compass. You will be supplied with turn by turn route notes and a detailed map so you will have no problems following the route each day.


We used handpicked, high quality B&B’s, guesthouses and country inns of typical Cotswold character. Honey coloured cottages, roaring log fires, comfortable country bedrooms and the warmest of welcomes are what we look for to make your stay extra special. We have included a few examples below to give you a better idea of what to expect.

Many B&B’s and hotels in the Cotswolds do not accept one night bookings for Saturday nights so occasionally we may book two nights over a weekend in one location and arrange return taxi transfers for you at no extra cost. We do this so that we can maintain the highest quality of accommodation.

Solo Walkers

This walking holiday is available to solo walkers but as we incur additional baggage transfer costs their is a solo walker supplement payable.

Single Rooms

If you require single rooms within your party we will always try and accommodate you subject to availability. A single supplement is payable.

  • Hand picked B&B, guesthouse and country inn accommodation in en-suite rooms
  • All breakfasts
  • Door to door baggage transfer
  • A detailed info pack, route notes and map for the lead booker
  • Emergency telephone support from our office in the event of a problem
  • Travel to the start or from the finish of the walk
  • Lunches, dinners, snacks and drinks
  • Travel Insurance
  • Personal Equipment
  • Taxi transfers or public transport should you need to skip a stage
  • Additional nights along the route

When To Go

You can start The Cotswold Round on any date between start of April and mid October, subject to availability. 

Please note as there are limited accommodations in Broadway which accept 1 night bookings, we may have to book your overnight stay in the village of Stanton, approx 4 miles before Broadway, or if that isn't possible we will book you for 2 nights in Winchcombe and include return transfers at no extra charge between there and Broadway. 

Getting to the Start

Rail: Train services connect London Paddington to Cheltenham Spa in 2hrs 15mins .

Bus: National Express coaches serve Cheltenham and take approx 3hrs 15mins.

Road: Road: Parking is at a premium in Cheltenham, if you are planning on leaving your car please contact your accommodation in Cheltenham and they will be able to suggest the most convenient
long term parking. Expect to pay about £5.50 per day for parking.

Please visit the Traveline Website or National Rail Enquiries for further information on public transport and timetables.

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.  Please ensure that you do not bring more than one bag of 20kg as if this occurs, the luggage transfer company will ask you to pay an additional fee for an extra bag which they will provide (£8) plus a charge of £6.00 per day for moving the extra bag. This additional payment, should it be necessary, needs to be made locally to the driver and in cash. We ask that all bags are ready for 9am and if not an additional supplement may also be payable locally to ensure that we can get your luggage to its destination on time.

If you are travelling from far afield and do have more than one bag it is possible to arrange for the extra luggage to be stored whilst you are on the tour for a fee of £25 per bag. These additional bags would be picked up from your accommodation at the start point of your tour and dropped off wherever you finish depending on the itinerary you are doing. Please contact us if you are interested in this option.

General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking/cycling gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

How fit do I need to be?
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What gardens can I visit in the area?
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What is the best way to get to/from the walk?
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What happens if I can’t walk a stage?


Day 1 Arrive Cheltenham Spa Day 2 Cheltenham Spa to Winchcombe 7.5 miles / 12 km Day 3 Winchcombe to Broadway 12 miles / 19.2 km Day 4 Broadway to Moreton-in-Marsh 13.1 miles / 21.1 km Day 5 Moreton-in-Marsh to Bourton-on-the-Water 10.5 miles / 17 km Day 6 Bourton-on-the-Water to Cheltenham Spa 15.5 miles / 26 km Day 7 Onward Travel

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