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8 days
  • self guided cycle
  • 7 nights in guesthouses and hotels
  • 7 Breakfasts





Trip Code: CMR

Trip highlights

  • Cycling Through the Heart of England
  • Quaint Stone Built Villages
  • Riding Across Rolling Hills
  • Biking Between Village Pubs and Old Coaching Inns

This holiday is intended to appeal to those who want a gentle introduction to cycling in the English countryside, as the Cotswold’s are hilly rather than mountainous. A week of marvelous rides will take you through one of the most beautiful and historic parts of England. Honey coloured stone villages, open wolds, wooded valleys and Roman roads are the background to pretty villages, “wool” churches, famous gardens, a Roman villa and welcoming inns. Your tour starts in elegant Cheltenham with its Regency buildings, beautiful gardens, and fashionable centre. Then a delightful ride takes you over the top of the Wolds and through Duntisbournes, crossing the River Dunt’s pretty fords. The route passes exquisite village churches with Saxon and Norman features. This is followed by an easy ride to Tetbury, an important medieval wool market town. You can stand inside the old market house and walk down the ancient Chipping Steps - the course for the Woolsack Races. The ride then continues through the Cotswold Water Park. From Barnsley you ride along the River Coln to Bibury - described by William Morris as the most beautiful village in England - and its famous row of weavers' cottages. Then down the scenic Windrush Valley, past Windrush village’s Norman church to Burford, an elegant town with its steep main street leading down to the river. Your ride also takes you to the Eastleach villages with their fine churches and historic footbridge, and to the Barringtons. After a visit to Chedworth Roman Villa, one of the best exposed Romano-British villas in Britain, the ride takes you through Northleach, another attractive wool town with a magnificent church, to the Slaughters, surely the most delightful villages in England. You stay two nights in a superb guesthouse in Guiting Power, a typical upland Cotswold village. On the final day you will visit the historic 15th century Snowshill Manor, take lunch at Broadway and enjoy the wonderful views from Broadway Tower. In the afternoon you can visit Sudley Castle once home to three of Henry VIII's wives, Katherine Parr, Ann Boleyn and Lady Jane Grey. Finally, free wheel down Cleeve Hill back to Cheltenham.

Trip Grading

introductory to moderate

More info about grading system

Traveller Rating


Arrival into Cheltenham Accommodation: The Portland Guesthouse, thought to have been built in 1836, is a Grade II listed building ideally located in the heart of Cheltenham. The property boasts seven en-suite bedrooms across four floors of the late Georgian building, retaining many of the original features.

Meals:  Nil

Make your way to the bike shop at Cheltenham Spa Train Station to collect your bikes. Ride 1: via Elkstone, the Duntisbournes & Daglingworth. Distance = 32 km/19.8 miles or 25.7 km/16 miles. This lovely ride is uphill at the beginning, but from Elkstone goes through easier, undulating countryside. The ride down the Duntisbourne valley is a treat. The churches at Elkstone, Duntisbourne Rouse & Daglingworth are particularly worth visiting. There are not many pub stops in the middle of the ride; you will need to visit The Green Dragon at Cockleford or the Highwayman on the A417. There are no other shops in Cheltenham. Ride 2: via Cowley, Sheepscombe, Painswick & Slad. Distance = 49 km/30.4 miles or 44 km/27.3 miles. This is an interesting, varied but hilly ride with attractive countryside and scenery and some famous towns and villages. You visit Painswick an elegant wool town, Slad, the home of Laurie Lee, the famous Cotswold author. Stroud the industrial centre of the valleys and Bisley another beautiful wool town. Although there are several steep hills the destinations are worth the effort. Accommodation: The Crown Inn is a 16th century stone inn overlooking the beautiful, wooded, Chalford Valley, your accommodation is 4 crowns.

Meals:  B

Ride 1: via South Cerney & Meysey Hampton. Distance = 35.7 km/22.2 miles or 28.15 km/17.5 miles This easy ride circles through South Cerney & the Water Park. It passes through several quiet villages & the flat south Cotswolds countryside. It finishes in Barnsley where the church & Barnsley House Garden are worth visiting. Ride 2: via Tetbury, Cherington, Ashton Keynes & Down Ampney. Distance = 53.2 km/33.1 miles. This easy ride visits Tetbury an attractive Wool town, then goes east to Ashton Keynes & the Cotswold Water Park. It goes through several quiet villages south east of Cirencester before going north back into the Cotwolds to the beautiful stone village of Barnsley. Accommodation: For two nights, the Catherine Wheel offers a warm welcome in its family-friendly 15th century Cotswold stone building with a lounge bar, restaurant and garden.

Meals:  B

Ride 1: a short ride to Cirencester Distance = 23.65 km/14.7 miles. This easy ride goes to Cirencester via Welsh Way & Whiteway, & returns via Preston & Ampney Ride 2: Fairford via the Coln Valley & the Eastleaches. Distance = 50 km/30.6 or 41.85 km/26 miles This beautiful ride goes down the Coln Valley, which has several typical, pretty, Cotswold villages. The Woollen Mill at Filkins is interesting, & you can buy some real Cotswold souvenirs. Fairford is a good place for tea, & the stained glass windows are a must.

Meals:  B

Ride 1: via Chedworth Roman Villa, Northleach & Notgrove. Distance = 35.5 km/22.1 milies or 26 km/16.4 miles. This is an enjoyable ride over undulating countryside. The Roman Villa is very interesting, and Northleach is an attractive ’wool’ town with a lovely church. Ride 2: via the Windrush Valley, Burford, Bourton on the Water & the Slaughters. Distance = 53 km/33 miles or 43.45 km/27 miles. This is an interesting, enjoyable and fairly easy ride. It goes through many picturesque Cotswold villages - Windrush and the Slaughters are particularly delightful. Burford is an attractive town & Bourton a busy tourist centre. Accommodation: Two nights at the Guiting Guesthouse a tastefully restored 16th century 4 star Cotswold stone farmhouse in the centre of a small and isolated typical Cotswold village that has allowed time to pass it by.

Meals:  B

Ride 1: A short ride to the Slaughters & Lower Swell. Distance = 23 km/14.3 miles This undulating ride goes through beautiful countryside & attractive quiet villages. Upper Slaughter is a lovely place to picnic & spend time by the ford on a fine day. Ride 2: to Snowshill & Chipping Campden via Blockley & Sezincote - with extensions to Broadway & Hidcote Manor Gardens. Distance = 42 km/26.3 miles, 45 km/27.9 miles or 56 km/35 miles The lovely ride goes across rolling countryside to Snowshill & Chipping Campden - two classic Cotswold towns. It can be extended to visit Broadway & Hidcote Manor Gardens. The ride is quite hilly, & even the minor roads round Chipping Campden get very busy at holiday weekends.

Meals:  B

Ride 1: via Winchcombe & Brockhampton. Distance = 28.6 km/17.8 miles or 27 km/13.5 miles This ride covers some beautiful countryside, with good views from the hills. It is quite hilly, particularly down into & up from Winchcombe, but it gives you a good knowledge of the Cotswold scarp! Winchcombe is well worth visiting, & it is easy to spend several hours there. Ride 2: via Northleach, Chedworth Roman Villa, Withington & Seven Springs. Distance = 41 km/25.5 miles. This ride goes through beautiful countryside, some attractive villages, and to Northleach - an important ’wool’ town - with an interesting ’wool’ church. The Roman Villa is fascinating. Drop your bikes off at the bike shop by 5.30 pm before making your way to your overnight accommodation.

Meals:  B

Trip concludes in Cheltenham after breakfast.

Meals:  B



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 7 breakfasts
  • 7 nights accommodation in guesthouses and hotels on a twin share basis with ensuite facilities
  • one piece of luggage per person transferred from Inn to Inn, not exceeding 20kg
  • Information pack including route notes & maps
  • Emergency hotline
  • GPX Files
  • 6 days bike hire, with E-bike hire on request (supplement applies, see below)
  • Panniers

  • Dinners, lunches & beverages
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip
  • Entrance fees
  • A supplement will apply if you are travelling solo or book a single room
  • Guide - this is a self guided holiday


Bike information


introductory to moderate  

Easy - Moderate. There is a choice of two routes each day 25 miles (moderate) or 15 miles (easy)

Departure dates

Daily from 18 Mar to 22 Oct


Please note that minor changes to your 2024 itinerary may apply.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from


Options & Supplements*
  • High Season Surcharge 2025USD$110
  • E-Bike SupplementUSD$200
  • Single Supplement 2024USD$990
  • Single Supplement 2025USD$1090
*Prices listed are per person

Frequently Asked Questions

Yes, 'wolds' are hills. On this cycling holiday in the Cotswolds there are a number of long ascents. You may consider hiring an e-bike, which we can support you with (supplement applies).

Yes it is possible to upgrade your standard bicycle hire to an electric bike on this cycling holiday in the Cotswolds. The fee for this is mentioned in the Departure Dates section on this page. Please request this with us as early as possible as there is a limited supply of e-bikes.

We would recommend a bit of map study before you undertake each ride. On most days, we give you two rides to choose from, so you can select the distance you are comfortable with that day or the sights that you are most interested in seeing.

We recommend that you do, just so that you can refer to them at times. However, they do not have to be out all of the time. If you have a reasonable phone or GPS unit, you can use the GPX tracks that we will send you. We would recommend bringing a waterproof map case to keep documents in.

Yes, all hire bikes should be looked after, otherwise the bike shop will have to charge for any damages or loss. You will need to refer to the accommodation provider each night to enquire about the best place to store and lock up bikes.

Yes, the bike shops that provide your bicycles are small local shops. They are unlikely to be able to just drop work on other bikes to attend to you. This means that you should be able to fix a flat tyre, adjust your brakes, and put a chain back on sprockets if it has jammed. We would recommend bringing a small bike multi tool. Normally the bike does not come with a full range of tools.

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