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          Cycling Tours in the Cotswolds

          We found 3 Holidays in your search for:

          Destinations (1)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 3 Holidays in your search for:

          Select Order Order By
          Destinations (1)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support
          Leisure Cycling in the UK Leisure Cycling in Cotswolds Road Cycling in the UK Mountain Biking in the UK Gravel Riding in the UK Family Cycling in the UK

          Arguably one of the most famous regions in England, the Cotswolds has so much to offer visitors, including cyclists. The rolling hills that range from the meadows of the upper Thames through to the Severn Valley are perfect for cycling on, with gentle climbs and swift descents, making it a real pleasure to explore.

          The Area of Outstanding National Beauty title it was awarded in 1966 could not be truer, especially when it comes to the idyllic towns and village that are dotted throughout the region. We love exploring the Cotswolds by bike and can’t wait for you to join us on our next cycling tour in the region!

          • All Cycling Holidays
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          • Cotswolds Cycling Holidays
          Select Order Order By
          Guided
          Guided
          United Kingdom

          Cotswolds - Bourton-on-the-Water

          Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

          $1,465 P.P.
          View Reviews
          2
          1
          2
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          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Cotswolds - Bourton-on-the-Water

          Guided Leisure Bike Tour

          E-BIKE HIRE AVAILABLE

          This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

          • Staying at Harrington House, a comfortable HF Country House in the centre of picturesque Bourton-on-the-Water
          • Three days guided cycling with an experienced leader
          • Enjoying leisurely rides through beautiful rolling countryside
          • Visiting the famous Cotswold market town of Stow-on-the-Wold
          • Visiting the historic village of Bibury, famous for its stone cottages which once housed weavers
          • Cycling through beautiful chocolate box villages
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Cotswolds to Windsor

          Self-Guided Leisure Cycling Tour

          Duration

          5 days

          Prices from

          $1,565 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Cotswolds to Windsor

          Self-Guided Leisure Cycling Tour

          E-BIKE HIRE AVAILABLE

          This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1565 per person.

          2027 $1600 per person.

          For a group of 4 or more we can offer the reduced rate of 2026 $1350 / 2027 $1380.

          You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • Tracing the River Thames from near its source all the way to Windsor
          • Didcot and its impressive railway heritage
          • The impressive Uffington White Horse & Dragon Hill
          • Beautiful wooded hills and green landscapes of the Chilterns
          • World famous Windsor Castle
          • Traditional pubs and award-winning English wines at the home of the Royal Regatta
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Cotswolds Explorer

          Self-Guided Leisure Cycling Tour

          Duration

          8 days

          Prices from

          $1,995 P.P.
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Cotswolds Explorer

          Self-Guided Leisure Cycling Tour

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1995 per person

          2027 $2035 per person

          For a group of 4 or more we can offer the reduced rate of 2026 $1850 / 2027 $1895

          You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • The famous Cotswolds market towns of Moreton-in-Marsh and Stow-on-the-Wold
          • Riverside relaxation in Bourton-on-the-Water, the “Venice of the Cotswolds”
          • Leisurely riding through beautiful rolling countryside
          • The historic village of Bibury, famous for its beautiful stone cottages
          • Cycling through charming chocolate box villages
          • Stately home of Blenheim Palace with 2000 acres of gardens and magnificent architecture
          Photo Highlights Dates

          Not sure which trip's right for you? Just ask!

          Get in touch and we'll help you find your perfect trip.

          Similar Destinations

          All Types of Cycling in the UK All Types of Cycling in the UK
          Scotland Scotland
          Europe
          Italy Italy
          Spain Spain
          Portugal Portugal
          Quote
          Saddle Skedaddle staff were excellent. Consistently high standards delivered year on year. Don't think I'd trust anybody else when booking a cycling holiday!
          Susan, Slovenia - Capital to Coast, Leisure Cycling Holiday
          Quote
          This was the best of the several organised bike tours I've been on by light years, and I'm now looking at doing other tours with Skedaddle.
          Jay, France - St Malo to Nice, Road Cycling Holiday
          Quote
          Everything about the Skedaddle operation was spot-on, great attention to detail both before and during the trip. I was impressed by all things on the trip, quality of food, route briefings, accommodation, maps. I could go on!
          Paul, Land's End to John O'Groats Classic - 16 Days
          Quote
          What one pays for is not having to worry about anything – and Skedaddle does an excellent job taking care of us. We haven’t tried the other tour companies but why bother when Skedaddle is top notch.
          Roger, France - Chateaux of the Loire
          Quote
          From the first day to the last, everything was fantastic. We never had to worry about anything. Hotels, van pick-ups, guides - you had it all covered!
          Carol and Jim - Peru, Cycling Holiday
          Quote
          On 10+ trips with Skedaddle they have always delivered great trips and service. You get what you pay for and Skedaddle are very good at providing well run cycling holidays.
          Rob, Italy - Sardinia Island Flavours
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          News, Reviews & Stories

          Cycle route in Dumfries and Galloway

          Skedaddle guide to the best cycle routes in Dumfries and Galloway

          Dave Shuttle, UK Route Developer and Guide, talks us through our cycle routes in Dumfries and Galloway and why our newest leisure cycling holiday should be on your wish list for next year.   Over the years, Dave has guided and scouted multiple cycling routes in Scotland, so who better to give us a breakdown ...

          Dave Shuttle - UK Product Lead at Saddle Skedaddle
          Dave Shuttle
          September 21, 2026
          Cycling on the Hadrian's Cycleway long distance cycle route

          7 Must-Do long distance cycle routes on the National Cycle Network

          If you’re looking for long distance cycle routes in the UK, you’ll likely have encountered the little blue and red signs marking the incredible National Cycle Network. For more than 30 years, Walk Wheel Cycle Trust has been the custodian of this network, developing and maintaining routes that make exploring the UK by bike more ...

          Amy McKie
          Amy McKie
          September 11, 2026

          Gallovidian Gravel – a New Gravel Scotland Adventure

          Gravel riding in Scotland just got better! Gallovidian Gravel joins Cycling UK’s growing collection of long-distance must-ride routes.   Since launching our gravel holiday range in 2023, we’ve sampled some of the best gravel riding in Scotland, so we were delighted to be involved in helping Cycling UK create a new off-road route in Dumfries and Galloway - 'Galloway Gravel Escape'. Working ...

          Dave Shuttle - UK Product Lead at Saddle Skedaddle
          Dave Shuttle
          July 25, 2026

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