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            Cycling Holidays 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

            Looking for Cotswolds cycling tours? This is one of the most famous regions in England, and the Cotswolds it 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, with gentle climbs and swift descents, making it a real pleasure to explore.

            Awarded an Area of Outstanding National Beauty  title in 1966, the Cotswolds are a jewel of the English country side, especially when it comes to the idyllic towns and villages  that are dotted throughout the region. We love cycling in the Cotswolds and can’t wait for you to join us on our next cycling holiday in this beautiful part of the UK! Discover more of the UK by bike.  

            • All Cycling Holidays
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            • Cotswolds Cycling Holidays

            Cycling in the Cotswolds

            The Cotswolds is one of England’s most rewarding regions for cycling, offering a blend lovely combination of rolling countryside, quiet lanes and postcard-perfect villages. Cycling in the Cotswolds is ideal for those seeking a relaxed pace, with gentle climbs and well-signposted routes that suit first time riders looking for gentle routes, or more experienced cyclists looking for a scenic escape. Whether you’re planning short 

            Cotswold cycling breaks or longer cycling holidays in the Cotswolds, the area delivers consistently beautiful riding within its gently rolling hills.
            Cotswolds cycling tours typically wind through honey-coloured stone villages, open farmland and historic market towns, making every ride scenic, in that quintessentially English way the Cotswolds are famous for. Popular Cotswold cycle routes connect charming destinations such as Stow-on-the-Wold, known for its traditional market square, and Bibury, famed for its picturesque weavers’ cottages along Arlington Row. Another highlight is Bourton-on-the-Water, often called the “Venice of the Cotswolds” thanks to its low bridges and riverside setting.

            From leisurely Cotswold cycle rides to fully supported cycling holidays, the region caters to a wide range of abilities. Its combination of manageable terrain and iconic scenery makes cycling in the Cotswolds an excellent choice for riders wishing to explore classic English landscapes.

            Cycling in the Cotswolds Image
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            Guided
            Guided
            United Kingdom

            Cotswolds - Bourton-on-the-Water

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,195 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds - Bourton-on-the-Water

            Guided Leisure Cycling Holiday

            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.

            Start DateEnd DatePrice p.p.
            15/06/2026
            Fully Booked
            19/06/2026£1,195.00
            24/08/2026
            Fully Booked
            28/08/2026£1,195.00
            • 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 Holiday

            Duration

            5 days

            Prices from

            £1,095 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds to Windsor

            Self-Guided Leisure Cycling Holiday

            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 £1095 per person

            2027 £1120 per person

            For a group of 4 or more we can offer the reduced rate of 2026 £945 / 2027 £965.

            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 Holiday

            Duration

            8 days

            Prices from

            £1,395 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds Explorer

            Self-Guided Leisure Cycling Holiday

            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.

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £1395 per person

            2027 £1425 per person

            For a group of 4 or more we can offer the reduced rate of 2026 £1295 / 2027 £1325.

            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.

            Cotswolds village

            What kind of cycling terrain is in the Cotswolds?

            The terrain across the Cotswolds is characterised by rolling hills, wide valleys and quiet country lanes, creating a varied but manageable riding experience for everyone. While there are some steady climbs, they are typically short and rewarding, making Cotswold cycling enjoyable rather than overly demanding.

            When is the best time for cycling in the Cotswolds?

            The best time for cycling holidays in the Cotswolds is between late spring and early autumn. From May to September, riders can expect longer daylight hours, mild temperatures and vibrant countryside, with wildflowers in early summer and golden tones emerging in the autumn months.

            What kind of bike is ideal for cycling in the Cotswolds?

            In terms of equipment, a hybrid or touring bike is ideal for most Cotswold cycle routes, offering comfort on both paved roads and occasional rougher sections. Road bikes  also work well for those focusing on distance, while electric bikes are a popular option for easing the climbs and making cycling in the Cotswolds accessible to a wider range of riders.

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            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.
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            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!
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            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.
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