Cycling holidays in The Chilterns

A cycling holiday in The Chiltern Hills may not, on first impressions, seem like a good option for those seeking a relaxing break. Luckily we have lots of experience in creating bike routes in this area and sufficient local knowledge to be able to offer some fantastic and almost traffic-free itineraries with only a few slopes. Most of the cycling is on quality bridleways, sunken lanes and towpaths. We do also offer a pretty challenging bike trip in the area for the more ambitious of you out there.

The Chilterns are an underrated part of England in our opinion. Just as pretty as The Cotswolds but nowhere near as touristy, you really feel like you’ve got away from it all - and yet it’s only a short train ride away from London. A visit to The Chilterns combined with a stay in London would leave you with a real appreciation of all the slices of English life.

In terms of landscape, the area is comprised of chalk downland, dry valleys, pastoral and arable fields, sweeping hills and ancient beech woodland. Choose to visit in May and you are likely to catch the breathtaking bluebells in the woods. Majestic red kites are an increasingly famous resident after a successful reintroduction programme. The Chilterns are fairly sparsely populated but peppered along the route are some very old and very charming towns and villages. At the southern end, The Thames cuts through the landscape making for some extremely dramatic and beautiful scenery.

Our Chilterns highlights

Hambleden Village

Midsomer Murders fans will want to visit the picturesque Hambleden Valley, as there are many villages nearby that have played host to a murder mystery!

Included in our Oxford and Thames royal palaces holiday


The chalk downlands and beech woods are home to millions of blue bells in April and May – the sight and scent make your heart soar!

Included in our Thames source to sea holiday

Chenies Manor

Chenies Manor House is one of the UK’s finest Tudor Mansion Houses with award winning gardens and original 13th Century features.

Included in our A Chiltern challenge holiday

Stoke Row

A beautiful, unpretentious country pub, the Crooked Billet is famous for its cooking, inglenooks, crackling log fires, flagstone floors and friendly atmosphere.

Included in our A riverside ride from Oxford holiday

Our Chilterns Cycling holidays

  1. Shakespeare's Way 7 nights

    William Shakespeare is widely considered to be the greatest dramatist of all time. His 37 plays feature inspired plots, remarkable poetry, brilliant…

    From £2,345

    Not so gentle / 6 or 7 nights / Self-guided / The Cotswolds

  2. A Chiltern challenge

    Following much of the 170 mile Chiltern Cycleway, this tour covers the entire Chiltern Hills area: from the Thames at Henley in the south west,…

    From £1,125

    Not so gentle / 4 or 5 nights / Self-guided / The Chilterns

  3. Thames source to sea

    Often described as 'liquid history', let the Thames lead you on a unique adventure through the heart and history of England. From its quiet source…

    From £2,690

    Not so gentle / 8 nights + / Self-guided / The Thames

  4. Oxford and Thames royal palaces

    The River Thames threads its way serenely through sleepy rural villages, pretty landscapes and through the heart of bustling historic towns such…

    From £1,690

    Gentle / Many durations / Self-guided / The Thames

  5. The grand tour

    We created this grand tour of England taking in many of its historic sights, to celebrate the 2012 Olympics. Like the games, the trip has been…

    From £3,050

    Not so gentle / 8 nights + / Self-guided / The Cotswolds

  6. A riverside ride from Oxford

    Oxfordshire boasts an idyllic and peaceful rural landscape. Quaint and pretty villages, the unspoilt Chiltern Hills, the charming meadows of…

    From £970

    Gentle / 4 or 5 nights / Self-guided / The Thames

Can't find what you're looking for?

Many of our trips are tailor-made, so tell us what you're looking for and we'd be delighted to design the perfect cycling or walking holiday for you.

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