Self Guided Walking Holidays & Cycling Holidays

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Walking through the Rapeseed fields


  • 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.

For more information on walking in the Cotswolds, you can Download our Free Guide to view offline or you can visit our Online Cotswold Information Page.

You can add extra nights at any point on the trail and can use taxis or public transport to shorten the walks if necessary.

Day 1: Arrive Cheltenham Spa

Cheltenham Spa is 86 miles west of London and trains leave London
Paddington every 30 minutes. The journey takes about two hours fifteen
minutes by train. Cheltenham Spa is England’s most complete Regency

On arrival take the time to wander the elegant pavilion, squares and
terraces, which are lined by distinctive Regency Townhouses complete
with intricate ironwork balconies and painted stucco facades. Cheltenham
enjoyed great fame for almost 100 years as a Spa town following the
visit of King George III and Queen Charlotte in 1788. Spa waters are
still available, but no longer the sole reason to visit Cheltenham.

Day 2: Cheltenham Spa to Winchcombe - 7.5 Miles

The walk starts at the Pittville Pump Rooms, probably the finest
example of Regency architecture in Cheltenham, set in the beautiful
Pittville Park.

Leaving Cheltenham you skirt the famous racecourse and soon climb the
Cotswold Escarpment at Cleeve Hill. The next six miles to Winchcombe
over Cleeve Common offer some of the most enjoyable walking on the
Cotswold Way. An area of open unimproved limestone grassland, the
walking is sublime.

Day 3: Winchcombe to Broadway- 10.5 - 11.5 Miles

Following the Cotswold Way you head north to the idyllic villages of
Stanton and Broadway. On the way you can visit Hailes Abbey and Stanway
House, some of the Cotswolds’ real gems.

Broadway has lured visitors for centuries and a stroll down the broad
tree lined High street is the perfect way to while away the evening.

Day 4: Broadway to Moreton on Marsh - 12.5 Miles

Your day starts with a steady climb to Broadway Tower, a unique
Capability Brown folly tower. Located at the second highest point on the
Cotswold Escarpment it offers one of the finest views in England.

After enjoying the tower enjoy a gentle stroll down to the honey
coloured cottages, tea rooms and gift shops of Chipping Campden.

Walking through the rolling hills of the
Cotswolds, wander through Broad Campden, Blockley and then to
Moreton-in-Marsh one of the most important market towns in the
Cotswolds, which still holds a weekly market on the wide main street.

Day 5: Moreton-in-Marsh to Bourton-on-the-Water- 10.5 Miles

As you leave Moreton-in-Marsh you can look forward to the most
delightful day of walking. Hopping between some of the prettiest
villages in the Cotswolds you soon reach Stow-on-the-Wold, an important
market town, whose streets are lined by art galleries, gift shops and

Don’t linger for too long as a few more miles through the rolling
Cotswold countryside bring you to Bourton-on-the-Water, probably the
prettiest village in Britain. Bourton is an absolute delight and is sure
to live up to your every expectation.

Day 6: Bourton-on-the-Water to Cheltenham Spa - 15.5 Miles

Following the river Windrush out of the Bourton-on-the-Water you are
quickly immersed in the Cotswold countryside. Naunton is the first of
several delightful Cotswold villages you visit. The day is punctuated by
wide open views, quiet woodlands and secluded valleys. The route leaves
the Windrush Way at Guiting Power and meanders through the countryside
to cross the Cotswold Way and finish at Prestbury, on the outskirts of

Day 7: Onward Travel 


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.


A delicious breakfast is included each morning. Lunch and dinner are not included. Most of your accommodation will be more than happy to provide a packed lunch on request. Dinner is available either at your hotel or at nearby pubs and restaurants.




Cornerways - Chipping Campden

Cornerways is a family run bed and breakfast excellently situated just 2 minutes walk away from the centre of Chipping Campden's famous High Street.







White Hart Inn - Winchcombe

The White Hart Inn is a 16th Century coaching inn offering comfortable accommodation in the heart of Winchcombe. Delicious evening meals are available at the 'Wine and Sausage' restaurant at the Inn.







Treetops - Moreton-in-Marsh

A warm welcomes is assured from Liz and Brian Dean at the Treetops Guest House situated in the small and friendly Cotswold town of Moreton-in-Marsh.







Cowley House - Broadway

Cowley House bed and breakfast is in a quiet location in the heart of one of the most beautiful of English villages and less than 50 yards from the many galleries, antique shops and restaurants in the High Street.







Broadlands - Bourton-on-the-Water

Broadlands Guest House, with an English Tourist Council four diamond rating, is situated in a quiet street, a few minutes level walk from the beautiful village centre and its many attractions.




More information on the Cotswolds

For more information on walking in the Cotswolds, you can Download our Free Guide to view offline or you can visit our Online Cotswold Information Page.


You can start The Cotswold Round on any date between start of April and mid October, subject to availability.To book select your preferred start date on the calendar.


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.


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.

Baggage 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 (approx. £5.00 per day, per bag). This additional payment, should it be necessary, needs to be made locally to the driver and in cash.

It is also very important that your bag is clearly labelled (and any additional bags). If they are not labelled we cannot guarantee that they will reach you at the next accommodation.

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.

Getting to/from Cheltenham Spa

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.


  • 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.


  • Single room supplement
  • Solo supplement
  • Additional nights along the route

We are often asked the following questions hope that you will find the following information useful.

Please don’t hesitate to contact us if you have any further questions.

How fit do I need to be?

The fitter you are the more you will enjoy your trip. The longer days can be shortened by using taxis or public transport to a maximum of 8 miles if you would prefer shorter days.

If you currently don’t enjoy an active lifestyle we suggest regular walking in hilly terrain supplemented by cardiovascular exercise for at least six months before your walk. A good gym or personal trainer will be able to draw up a personalised training programme.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the Cotswolds are extremely popular. If booking at short notice, we will always try and accommodate your plans.

Can I combine my Cotswold holidays?

Depends on which guidebooks/maps/route notes you use for your particular trip, it can be possible to combine them. Check with your destination specialist, and they will be more than happy to let you know if your itinerary is possible.

What gardens can I visit in the area?

We would recommend Blenheim Palace, the birthplace of Sir Winston Churchill, and Hidcote, famous for its rare trees and shrubs. Click here for a full list of Gardens and Arboreta in the Cotswolds.

What ruins/history/country houses can I see along the way?

There are many houses and historical monuments throughout the Cotswolds, and what you can see depends on the itinerary you are doing. There are historic houses, rustic ruins and many museums for you to explore. Click here for a full list of Historic Houses and Museums.

What personal equipment do I need?

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. You can download a full equipment list from the downloads page of our website.

When is the best time of year?

We offer this trip between the beginning of March and the end of October. In our opinion, there is no bad time for walking in the Cotswolds but would especially recommend the spring and autumn. 

What is the best way to get to/from the walk?

We recommend you travel by train to Cheltenham on Spa. You can take a train from London Paddington in 2nrs 15 mins. Alternatively, the national express coach takes 3hrs 15 mins.  parking is at a premium in Cheltenham so we would recommend taking public transport.

Am I able to take my dog?

Unfortunately we are unable to accommodate walkers with dogs as many of the accommodation providers we use do not accept pets.

What happens if I can’t walk a stage?

You can use local bus services or local taxis to continue to your next overnight stop.

Terrific Time


We enjoyed the walking which was long and doable. The accommodations were comfortable, easy to get to and interesting - each and every one in their own way! The navigation app was a lifesaver!




Challenging, but worth it!


This was a fantastic tour of all things Cotswold! Great distance between overnights, easy-to-follow directions, and helpful travel agents!

The Hiking Fam

Ohio, USA


Beautiful scenery and tour


Great to have accommodations, paths, turn by turn directions, luggage moved. MACs mileage significantly different than reality - 25-35+% more than was listed on the MACs information - so if you were planning to walk a day of 19km from Macs info - the walk was actually 26-28 km. This should be accurate so folks can plan the walk with respect to weather, energy level etc. You are asking for a bottom line below - I think you get the mileage correct so this is accurate and this is a good tour (or you adapt if you feel the mileage is too much) but incorrect mileage is significant enough to cause concern and I could not recommend as is. One hotel facility would not recommend- no community area and very tiny rooms - otherwise facilities were great, transfer of luggage seamless. Thank you.


Boston MA


Excellent Experience


The accommodation in Broadway wasn't clean and the place was a little run down- but the owners were very nice


Princeton NJ


Cotswold Round


Had a great 5-day walk in the Cotswolds. Enjoyed the scenery and the many interesting and beautiful medieval churches, abbeys and towns.


Estes Park, CO


One item of my bucket list-DONE!


We were very pleased with the organization. We received our travel information long before we left for the walk. The majority of the B & B's were lovely.

no nickname



Very picturesque


We thought the trip was well organised, baggage transfer worked without a hitch. Accommodation was all very good. The routes on the whole were well planned and scenic varying from day to day. Just the odd left and right mix up but nothing an OS map couldn't sort out. But after all the rain in April many of the fields by the gates were thick slippy mud and one hill the last day was virtually impassible at one point I sunk up to my knees (not Joking) in boggy mud and we won't even mention the horse breathing in my ear as I tried to escape the field !




Fantastic Walk, well organised, very happy!


This is a well organised walk through beautiful countryside and stunning villages. everything organised by Macs Adventures worked well and their choice of accommodation was perfect for us. This is our second trip with them and we will use them again. Highly recommended.


Bucks, UK


Cotswold Round


Superb walk in good autumn weather with splendid accommodation in beautiful Cotswold towns. One problem however; the route notes need updating. e.g. Travis Perkins garden centre in Cheltenham is now a housing estate, most of the Gustav Holtz way markers are not there, and not all the other waymarks mentioned are there.




Relaxing walk in beautiful, quiet countryside


First stretch was a bit of a puzzle where to head, but that is part of the fun. Good distances. Although a bank holiday was included, we were on all walks almost by ourselfs in the endless fields with sheep, cows and flowers (end of May), Truly getting away.




The Cotswold Round

4.4 16


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