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Self Guided Walking Holidays & Cycling Holidays

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Short walking break in the Cotswolds


  • Strolling through the picturesque Cotswold villages.
  • Relaxing in handpicked, luxurious and welcoming accommodation
  • Discovering the history of the area through abbeys, ruins and the glorious Sudeley Castle.
  • Enjoying some of the best views of the quintessential English countryside.

Experience the highlights of the Cotswolds Way on this walking escape. This tour explores chocolate box Cotswold villages such as Broadway and Stanton as well as taking in interesting historical sights and spectacular views in quintessentially English countryside.

Your walking break starts in Chipping Campden, arguably one of the loveliest of the Cotswold towns with it’s typical honey coloured architecture. You begin with a climb onto the escarpment where you will be rewarded with some fine views, before enjoying the welcome diversion of Broadway’s tearooms and finally arriving at the idyllic village of Stanton.

Heading on to Winchcombe, you will pass through rolling hills and some steep ups and downs as well as historical sights of interest such as the medieval Hailes Abbey and the Iron Age hill fort Beckbury Camp before arriving in the bustling town of Winchcombe.

On your final day’s walk, after a possible visit to the magnificent Sudeley Castle, some of the best views of the walk beckon with delightful open walking over Cleeve Common and outstanding views from the Cotswold escarpment.

Hand-picked overnight accommodation in high quality Hotels, B&B’s and guesthouses, daily door to door baggage transfer, maps, route notes and emergency support are included in your walking break with Macs Adventure.

Day 1: Arrive Chipping Campden

Chipping Campden is arguably the loveliest of the Cotswold towns and a great place to start your walk. A two hour train journey from London to Moreton-on-Marsh and a 6 mile taxi or bus brings you easily to the start of your holiday.

Day 2: Chipping Campden to Stanton - 10 Miles

Leaving the honey coloured architectural beauty of Chipping Campden behind you climb immediately onto the escarpment where Dover’s Hill and then Broadway Tower reward with fine views. The tearooms of Broadway are a welcome diversion before heading back into the hills. The idyllic village of Stanton welcomes you at the end of the section. Stanton is a typical small Cotswold village with evening meals available from the local pub.

Day 3: Stanton to Winchcombe - 7 Miles

Tearing yourself away from the beauty of Stanton, you soon reach the hamlet of Church Stanway. The ornate guesthouse of Stanway House distracts from the climb to Stumps Cross which follows. The Iron Age hill fort Beckbury Camp and medieval Hailes Abbey are both of interest before you reach the hustle and bustle of Winchcombe. Winchcombe was once an important Saxon settlement and it’s folk museum and the gargoyles of the Church of St Peter are of interest. The ancient Saxon borough of Winchcombe offers plenty of facilities for walkers and holiday makers. There are several tea rooms serving typical English afternoon tea as well as several pubs .

Day 4: Winchcombe to Dowdeswell - 11 Miles

The last section is a scenic and historically interesting one, beginning with a six mile stretch to Cleeve Hill. The magnificent Sudeley Castle is soon followed by a Roman Villa and Belas Knap, a huge Neolithic burial chamber. Continuing on to Dowdeswell you will enjoy a series of outstanding views from the Cotswold escarpment. You will be staying overnight in the town of Charlton Kings, near Dowdeswell Reservoir.

Day 5: Depart Dowdeswell/Charlton Kings

If you have parked your car in Chipping Campden then you will need to get a bus from the nearby town of Cheltenham back to Moreton-on-Marsh or Broadway and then a taxi or bus will take you back to Chipping Campden. Cheltenham is also well linked by train services to London and Bath.


One of the highlights of this tour is the high standard of the accommodation. You will stay in carefully selected 3 or 4 star B&B’s, guesthouses, country pubs and small hotels. Your room will always have an ensuite or private bathroom. A delicious breakfast is always included.

Alternative accommodation

During the high season, you might be booked into alternative accommodations which are not listed in the description. Any alternative accommodation will be of the same or better standard as those described.

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.

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.


A hearty 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 accommodation or at nearby pubs or restaurants.

Useful Websites

Cotswold Way National Trail Website

Amusing Diary of The Cotswold Way

Cotswolds Area of Outstanding Natural

Tourist Guide to The Cotswolds




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.







Shenberrow Hill - Stanton

Shenberrow is an attractive country house which offers luxury accommodation in the lovely little village of Stanton.







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.







Detmore House - Charlton Kings

Detmore House is a period property set in extensive grounds with spacious ensuite rooms. It is also very close to the towns of Cheltenham, Gloucester and the Cotswold Way making it an ideal base to explore the area.




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


A hearty 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 accommodation or at nearby pubs or restaurants

General Information

The distances are approximations of the recommended routes. Please be prepared by packing all essentials, for example proper rain gear (jacket and pants), sun hat, and sunscreen.

Baggage Transfers

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.

Getting to/from Chipping Campden

 Rail: Train services connect London to Moreton-on-Marsh (2hrs) and Birmingham to Stratford-upon-Avon (1hr). Taxi or bus services are available for the respective 6 or 12 mile last leg to Chipping Campden. Road: National Express coaches serve Bath, Cheltenham and Broadway. Unsecure on-street parking is available in Chipping Campden.

Getting from Dowdeswell/Charlton Kings

Rail: The nearest train station to Charlton Kings where you will be staying on your last night is Cheltenham which is approx 3 miles away. The train from Cheltenham to London takes approx 2 hours or approx 1hr 30 to Bath.

If you have left a car in Chipping Campden getting back from Cheltenham on public transport takes about 3 hours. Please visit Traveline  for further information.


  • Hand picked B&B, guesthouse and small hotel accommodation in en-suite rooms.
  • Door to door baggage transfer.
  • A detailed info pack, guide book and map for the group leader.
  • 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.


  • Single room supplement - If you require a single room in your party there is a single room supplement payable for each single room required.
  • Solo walker supplement - If you are walking solo there is a solo walker supplement payable to cover the additional baggage transfer costs. This is in addition to the single room supplement.

We are often asked the following questions by walkers planning The Cotswold Way and I 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?

This walk is graded as easy to moderate because the daily distances are an average of 9 miles but it does involve some steep ascent and descent from the escarpment. If you currently don’t enjoy an active lifestyle we suggest regular walking in hilly terrain supplemented by cardio vascular exercise for at least 6 months prior to your walk. A good gym or personal trainer will be able to draw up a personalised training programme.


This walk is waymarked clearly througout. However, in some sections the waymarking can become a bit unclear so we recommend that you are able to navigate using a map and compass to enjoy this walk at it's best.

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.

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?

The Cotswold Way is sublime at any time between the beginning of April and beginning of October although my personal favourite time of year is the spring.

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.

We had a fabulous walk


An all round lovely vacation! People were welcoming and interested in our walking experience. The walk was a challenge at times but we were able to use the option of public transit on 2 occasions when it was just a "little too much" for us that day. Scenery was stunning. Weather was good. I'm a vegetarian...the food was delicious and nutritious...just what one needs for a days walk. Thanks again Macs for a great adventure.

sharmaine and gerrit


An enjoyable country interlude


Hiking in the Cotswolds broke up our longer stay in London. We enjoyed each day on the Cotswold Way and appreciated the friendliness of everyone we encountered. Our B&B's were just right and our luggage was always waiting when we arrived. Thanks to MacsAdventure for doing exactly what you said you would do.

Susan C.


Seven days of fun exploration


We are an avid walking couple in our mid-sixties. This trip gave us a wonderful way to explore a new area and to catch up with old friends who met up with us at various points. We liked all the accommodations except one and were impressed with the friendliness and helpfulness of hosts along the way. The baggage transport was flawless. If doing the entire Cotswold Way I would recommend including two rest days to break things up and have a chance to linger and poke around the beautiful and interesting villages.

Green Mountain Hiker

Vermont, USA

its a challenge!


Our first experience of a walking holiday. Beautiful views ( we were lucky with the weather!) Wonderful Cotswold villages. Well signposted. Some fairly steep hills and slippery muddy paths but if you are well equipped its fine. Some of our booked accommodation left a lot to be desired. The itinerary provided by Macsadventure did not match the local experience in a number of cases, please be aware! I have given them detailed feedback, hopefully they will update their information. I couldn't recommend this holiday done in this way, when you most need good hospitality at the end of the day its often sadly lacking !



Beautiful countryside, interesting villages and so much hist


Initially Macs sent the materials in error to all three couples.Baggage courier service was excellent.Our first night in Chipping Campden we were booked directly over the band that was playing. We had several good b&b,two or three excellent,and two not so good.Mileage indicated was short vs our GPS. Thank you to Macs accommodating our group of six and keeping us together almost all the overnights.


North Carolina

I would recommend this holiday (Cotswold Way)


I would recommend this hike however it was more challenging than expected. All the accommodations were good however there were a couple of times when the pub was not easy walking distance to the accommodation which was an issue. Also two days were quite short when they could have been a bit longer to balance out the hike a bit more.

Nic & Sharon - hiking adventurists


Fantastic Trail!


This was my first time using Mac's Adventures and the second time I have completed a self-guided walking tour. Mac's was great- no hiccups and everything ran smoothly. They had a good reputation on the trail which means a lot. I would and will absolutely use them again for future walks. So we are a mildly active couple who took the longest trip possible to accommodate our lackadaisical fitness level. We loved our 7 mile days and we managed our longer days with some ibuprofen for sore feet and the promise of a pint at the end of the trail. The trail itself is truly beautiful and we were constantly impressed even though we come from an area with amazing trails. There was very little road walking and so much variation of scenery- well signed and first class trail. I was occasionally chagrined when it would send us straight up a steep hill without a switchback in sight. This trail never met a hill it didn't decide to climb and any monument you could see high up in the distance you knew for sure you would be ascending shortly to the base. I would recommend adding plenty of elevation hiking to your preparations if you are not used to it. As for the accommodations, I loved all of the old inns and small hotels we stayed in. I think one of the big differences about hiking in England versus other parts of the world are the laws about public pathways and right to roam which means that a path can go right through privately owned fields and farms without being diverted to streets and forestry roads. This creates a very special walking experience with constantly beautiful scenery, the regular accompaniment of sheep, cows, and horses, and nice soft turf to walk in rather than bruising concrete. Special shout-out to Chipping Camden, Broadway, Winchcombe, and Bath. Absolutely gorgeous places not to be missed.

The Lazy Walkers

Olympia, WA USA

Nature at its best!


I would definately recommend to anyone to book an adventure with Macs, we took on the 5 night 4 day walk on the Cotswald Way, the scenery is stunning, accomodation was great and the towns are so quaint, the best of the best. Just make sure you do get fit before undertaking and have good hiking boots and wet weather gear. Our time in the Cotswalds had people questioning and remarking on where are you, I want to do that, it looks great! The greeness of the countryside blows your mind, give it a go!

Steve & Leslee

Tumbi Umbi NSW Australia

Challenging Walk


Even though we had read about how hilly the Cotswolds are we weren't expecting it to be so wet and muddy which made it even more challenging. Even so the area is beautiful and we enjoyed every day. The accommodation was also very good and varied, we were well looked after.

Wet walker

Melbourne, Australia

Two grumpys on the Cotswold Way for seven days


Firstly, sincere thanks to Macs Adventures for helping us to organise this walk. The organisation was first class and the accommodation (B&Bs, inns and small hotels) was ideal. Last year we walked the Cumbria Way and thought, as we're no spring chickens, that we would do the Cotswold Way because it would be easier. How wrong we were! The Cotswold Way is 102 miles long, which, over 7 walking days is not a problem. But when you add on a total of 10,000 feet of climbs onto the hills (in small chunks of 200 or 300 feet) it makes an easy walk quite strenuous. Nevertheless, what a week! The walk is well sign-posted, and the maps are easy to follow. Two minor mistakes meant that we walked 400 yards further than we should have done; not bad for 102 miles. The countryside is some of the best that England has to offer and the views from the top of the wolds are spectacular. And the icing on the cake is that, apart from the final day, there's a pub on the route every lunch time to enable you to quench your thirst. Take a week off from tasteless lagers and try some real cider - brilliant! In summary, it really was a beautiful walk and memorable week. Yes, you need to be fit, but, as two old grumpys can testify, you don't need to be Charles Atlas. So go for it!

Two grumpys



Cotswold Way Walking Holiday

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