Published: 04.05.2020

Guide to Cottage Holidays in the Chiltern Hills

Chiltern HillsThinking of taking a cottage break in the Chiltern Hills AONB? 

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What the Chiltern Hills AONB Offers for Cottage Breaks

Covering parts of Bedfordshire, Bucks, Herts and Oxfordshire, the Chilterns are an area of outstanding natural beauty stretching from near Wallingford in Oxfordshire up through and around areas in Hertfordshire, greatly benefiting towns such as Amersham, Berkhamsted, Tring, Wendover and other local villages with beautiful vistas of surrounding hilly countryside.  If you are searching for a base in beautiful countryside yet within a commutable distance to London, a self-catering stay in the Chilterns may be perfect for you.

The Chiltern hills come to an end at an impressive peak at the stunning Ivinghoe Beacon and Dunstable Downs near Luton.  The Chilterns are made up of rolling hills and at their peak they reach 250 metres in height.

Many pleasant and attractive market towns are dotted throughout the Chilterns, each with their own charm and character.  The most idyllic hamlet in the area without a doubt is Ashridge which is a small peaceful village at the foot of the Chiltern Hills, very near Ashridge Forest.  Read through the details of the attractive Chiltern towns below, you may want to find somewhere to stay in one of these towns or may prefer to find a country cottage nestled deep in the Chilterns countryside.

A great many towns in the Chilterns can be reached by train from London in less than an hour, making the Chilterns a perfect getaway for those seeking a bit of peace and tranquillity during a self catering holiday within an easy commute of London.  To get the most out of a visit to the Chilterns though and to explore hidden gems such as Aldbury it’s best to travel by car.

Many enjoy the beauty of the Chilterns and take walks or cycle rides in the forests such as Wendover Woods or Ashridge Forest whilst enjoying a cottage holiday in the beautiful countryside.  Recently there have been a number of  campaigns about the importance of protecting this beautiful part of England due to the proposal for a High Speed railway to pass through this green area.  The Chilterns are home to many deer and birds such as red kites which various trusts work to protect and are understandably campaigning to preserve the beautify and rich wildlife here.  If you enjoy doing a spot of wildlife watching on your cottage holiday, then the Chilterns forests are a definite place that you should visit.


Recommended Towns & Villages to Visit in the Chiltern Hills

The below towns and villages stand out as quaint, picturesque places and are worth visiting.


Aldbury is a pretty little village which sits at the foot of Ashridge forest.  This village is unspoilt and a well kept secret.  There is a small village green with a duck pond and a number of pretty oldey worldey style houses.


Amersham itself is a busy large town with little to recommend it for visitors in terms of picturesque scenery.

Old Amersham

Old Amersham though is a world apart.  Old Amersham nestles at the bottom of a hill, near Amersham but is quite separate from Amersham.  Old Amersham is picturesquely nestled in the Chiltern countryside.

Old Amersham is very pretty and there are a number of historical buildings there which centre around one long very wide elegant high street.  The pavements are mostly cobbled and the high street dates back to the days of coaching inns where Old Amersham was one of the first stop off destinations for journeys between London and Birmingham.  There is an ancient Market Hall which is still used for markets today and Old Amersham’s high street is lined with designer shops, craft shops and restaurants.  There is a museum of an original tudor house from which you can pick up walking tours of the old town on certain days.


Picturesque Berkhamsted for self catering holidaysBerkhamsted is a small busy picturesque market town in Hertfordshire.  Berkhamsted has an elegant busy high street with plenty of cafes, pubs and restaurants.  Berkhamsted is a historically rich town where you can visit a ruin of a castle which dates back to the 11th to 13th centuries.  Another of Berkhamsted’s charms is its attractive canal.  The Grand Union canal runs through Berkhamsted and barges can be seen drifting slowly by, along with ducks and swans.
The National Trust’s Ashridge woods can be found just a few miles from Berkhamsted for those who enjoy quiet forest walks away from it all.

Berkhamsted is around 30 minutes by train from London Euston and is located near to the towns of Tring and Hemel Hempstead.

Ashridge forest is situated a few miles from Berkhamsted. 


The Chiltern hills are very noticeable around Chesham town centre and greatly add to the appeal of the town.  Chesham is a small town, which although reasonably attractive, lacks the appeal of other prettier more up market towns such as Berkhamsted or Tring.


Ivinghoe is a small village situated near Ivinghoe Beacon and the Dunstable Downs.   There is a village green and a pretty church and a number of Tudor style historical buildings.  A little tea shop has recently opened up in Ivinghoe and is a welcome addition for those looking to explore the area.

Pitstone Windmill is on the outskirts of town and can be reached by foot but due to the lack of ease of access it is best to drive.

Picturesque Ivinghoe Beacon can be found just outside the village of Ivinghoe.


Tring in the ChilternsTring is a picturesque market town in Hertfordshire.  The beautiful Chiltern Hills skirt around the town of Tring.  The Woodlands Trust’s Tring Park can be reached from the edge of the town and has wonderful walks across the countryside.  Tring also has its own National History Museum with a multitude of stuffed animals, birds, insects, fish and reptiles from Lionel Walter Rothschild’s original private collection.  This museum continues to fascinate both old and young visitors.  Entry is free currently but a donation is requested.

There is a pretty high street with a variety of shops, pubs and restaurants.

The Grand Union Canal runs by the outskirts of Tring.
Tring is around 40 minutes by train from London Euston and Tring Station is located around 1 mile from the town itself. Aylesbury and Berkhamsted are towns both located near Tring.


Wendover is a picturesque oldey worldy town near Aylesbury in Buckinghamshire.  The town is surrounded by the Chiltern hills, giving Wendover something of an alpine feel to it.  Pretty old buildings line the High Street and there are lots of gift shops and restaurants.  One gem on Wendover High Street is the lovely chocolate café where you can enjoy tea and chocolates or chocolate cake.

Wendover Woods can be found on the outskirts of Wendover, high up on the hills, with amazing views over the surrounding countryside.  There are tracks where you can enjoy a walk or a cycle.  If you like to ‘monkey’ around you may be interested in finding out about Go Ape’s high adrenaline course high up in the trees.  There is a Forest Café where you can buy a welcome cup of tea.

Ivinghoe Beacon

Historically Ivinghoe Beacon was an ancient signal point.  Nowadays many visit to walk or fly kites at Ivinghoe beacon where you can enjoy spectacular views of Bedfordshire and Hertfordshire from quite some height.

Dunstable Downs

The Dunstable Downs are an area of outstanding natural beauty.  There is a visitor centre run by the National Trust at Dunstable downs.  The Dunstable downs are popular with walkers but also with those with a love of kite flying and with those who enjoy the thrill of paragliding.   Outstanding views greet you on the Dunstable Downs of the Chilterns, Bedfordshire, Hertfordshire and Buckinghamshire. 


Wherever you decide to stay in the Chilterns, the towns and villages listed above are in our opinion the most picturesque for cottage holidays in the Chilterns.  Whether you are seeking a traditional country cottage or something more traditional we hope you find what you are looking for here.

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