Cycling Holidays in the Cotswolds

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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 holiday in the region!

Guided

United Kingdom

Cotswolds - Bourton-on-the-Water

Guided Leisure Bike Tour

Duration

5 days

Prices from

$1,640 P.P.

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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.

Start Date	End Date	Price p.p.
13/04/2026	17/04/2026	$1,640.00
15/06/2026 Guaranteed	19/06/2026	$1,710.00
24/08/2026	28/08/2026	$1,710.00

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

United Kingdom

Cotswolds to Windsor

Self-Guided Leisure Cycling Tour

Duration

5 days

Prices from

$1,640 P.P.

View Reviews

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 $1640 per person

For a group of 4 or more we can offer the reduced rate of $1425 (2026).

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

United Kingdom

Cotswolds Explorer

Self-Guided Leisure Cycling Tour

Duration

8 days

Prices from

$2,095 P.P.

View Reviews

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 $2095 per person

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.

Cycling Holidays in the Cotswolds

Cotswolds - Bourton-on-the-Water

Guided Leisure Bike Tour

Duration

Prices from

Cotswolds - Bourton-on-the-Water

Guided Leisure Bike Tour

E-BIKE HIRE AVAILABLE

Cotswolds to Windsor

Self-Guided Leisure Cycling Tour

Duration

Prices from

Cotswolds to Windsor

Self-Guided Leisure Cycling Tour

E-BIKE HIRE AVAILABLE

Cotswolds Explorer

Self-Guided Leisure Cycling Tour

Duration

Prices from

Cotswolds Explorer

Self-Guided Leisure Cycling Tour

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

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Cycling Holidays in the Cotswolds

2025

2026

2027

2025

2026

2027

Cotswolds - Bourton-on-the-Water

Guided Leisure Bike Tour

Duration

Prices from

Cotswolds - Bourton-on-the-Water

Guided Leisure Bike Tour

E-BIKE HIRE AVAILABLE

Cotswolds to Windsor

Self-Guided Leisure Cycling Tour

Duration

Prices from

Cotswolds to Windsor

Self-Guided Leisure Cycling Tour

E-BIKE HIRE AVAILABLE

Cotswolds Explorer

Self-Guided Leisure Cycling Tour

Duration

Prices from

Cotswolds Explorer

Self-Guided Leisure Cycling Tour

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

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