
Holiday houses in Chiltern Hills
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Top-rated holiday rentals in Chiltern Hills
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The Nook at Pine View - set in Roald Dahl Country
The Nook at Pine View, is set within the Chiltern Hills in a designated Area of Outstanding Natural Beauty. In the heart of "Roald Dahl Country", Cobblers Hill is famously written within the pages of "Danny Champion of the World". The Nook benefits from stunning rural views and the peace & quiet of country living but with easy access to award-winning restaurants, pubs & cafes all just a short drive. A 45 min train to London. The surrounding area has some renowned country walks and cycle paths.
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Escape to Country Living at its Finest!
Escape to the country and unwind at this charming, elegant cottage in 2 acres of lovely gardens with swimming pool, tennis badminton and table tennis, and county walks starting from your door. Located on the edge of the award winning village of Cuddington, walk to the thatched roof pub for drinks and dinner or village store for supplies and news papers. Only 10 minutes drive to the bustling market town of Thame, 35 minutes to Oxford, 40 minutes to London by train and 45 minutes to London LHR.
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Beautiful cosy Scandi-barn in Chiltern market town
A beautiful, calm and cosy space designed to feel like a home from home. Lovingly updated and modernised, whilst retaining original character and features to create a unique guest experience. Uber-clean and free from clutter, everything looks & feels fresh for each stay. The kitchen, carpets, paintwork, doors, windows and VELUX roof-lights have been replaced or updated recently. Located with a parking space in a secure, gated courtyard just moments from the town centre of Princes Risborough.
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The Old Music Studio - retreat with tennis court
A stay in our former music studio is an immersion in nature. After a walk in the Chilterns and a fireside drink at a country pub, relax on the large comfortable sofa and watch the wildlife in the meadow from the warmth of this cosy retreat. If you’re feeling energetic, play tennis or pickleball on our court or cycle the Phoenix Trail - (Bikes/E-bikes by arrangement.) A perfect hideaway for a romantic break, recreational weekend, peaceful remote working or just recharging your batteries.
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Idyllic escape - wild swimming, stunning walking
Tucked into the Chilterns, The Old Stable is a bright, vaulted 17th Century barn conversion. Lavished with love & attention to detail - inside you'll find a king sized bed, a huge power shower, underfloor heating, a fully equipped kitchen (with Nespresso and dishwasher) and Smart TVs with Netflix. Step outside to find a croquet lawn, tennis court, hammocks and a natural swimming pond. Footpaths run straight from the property. We were on BBC's Countryfile! 3rd May on BBC iPlayer for a peek.
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17th Century Barn in quiet country village
A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.
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The Woodland Retreat With Private Hot Tub Spa
Our brand new listing is a truly unique woodland retreat with a luxury super king bed, dedicated private hot tub & 65 inch tv. Perfect for a couple get-away, this place will take your breath away. Nestled in our remote private woodland on our farm estate this little gem is in touch with nature yet fully fitted with all the home comforts you need. Additionally the woodland retreat includes: 1x private bathroom, a fully fitted outdoor kitchen, WiFi and a bespoke oak outdoor dining table.
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Chilterns Country Escape
Perfect for your escape to the country, a self-contained annexe set in the Area of Outstanding Natural Beauty that is The Chilterns, yet only a short drive from the M40 motorway, London and Oxford. There is everything that you need, whether for overnight or a longer stay, with a well equipped kitchen. Come for the peace and quiet, admire the wildlife, explore the unspoiled countryside on foot or by bicycle or enjoy the wealth of top class local restaurants and tourist attractions.
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The Coach House, rural location in central Bucks
The Coach House is a large, spacious cottage (2,000 sq ft) with three double bedrooms which has been recently renovated . It is located between the villages of Long Marston and Wingrave in a quiet, rural location. It is close to Tring and the Chiltern Hills and London is easy to get to from Leighton Buzzard station (35 mins to Euston) which is 15 minutes away. Plenty of good pubs in the vicinity, varied walks, National Trust properties, Bletchley Park museum and Whipsnade Zoo.
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The Stable Lodge
The Lodge is light, airy and modern, whilst providing original character and features. An ideal getaway for couples, those visiting family and friends, or somewhere to base yourself for a weekend of walking in the chilterns; this cosy, self-contained lodge is perfect for those looking to get away from it all. Set on a working stable yard surrounded by private ancient woodland accessible to guests. Private fenced garden, however not secure on one side for a determined dog.
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Gardeners’ Cottage (Georgian stable conversion)
An entirely self contained cottage, recently converted from a Georgian stable and gardeners’ lodge. While adjacent to the owners property it is entirely separate, with its own secure parking and EV charger. Located in a small village, with two pubs on doorstep. Market town of Wallingford (setting for “Midsomer Murders”) is short walk, many amenities including boat rides on the River Thames an outdoor heated pool (summer), great restaurants and shops including Waitrose.
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Fabulous Farm House in Skirmett
Valentine Farm House is newly refurbished to the highest standard and provides a wonderful base for a quick break or a longer stay, in the picturesque village of Skirmett, situated in the Hambleden Valley. Immerse yourself in country living in the Chilterns and enjoy the fantastic atmosphere of rural life. With horses to admire, right on your door step and unlimited walks, bike rides and local pubs to pop into, you're going to be falling in love with Valentine Farm.
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Popular amenities for Chiltern Hills holiday rentals
Other great holiday rentals in Chiltern Hills

Modern Self-Contained Detached Studio in Village
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Serene & Private Annexe in Village Centre
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Honey Barn - Stunning 4-Bed Rural Paradise
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Kop Hill Barn in the heart of the Chilterns
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Idyllic stable in the Chilterns
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Straw Plaiters Cottage
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Cosy Country Self Contained Annex
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Modern6bed, 30min Airport,London Legoland Windsor
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Frequently Asked Questions
Where is Chiltern Hills located?
Chiltern Hills is situated in southern England, stretching across parts of Buckinghamshire, Hertfordshire, Oxfordshire, and Bedfordshire. The area is known for rolling landscapes, traditional villages, and scenic woodlands within the United Kingdom.
When is the best time to visit Chiltern Hills?
Late spring and early autumn are often recommended in Chiltern Hills for comfortable temperatures and abundant greenery. Many visitors enjoy the mild climate between 44–72°F (7–22°C), and local trails and woodlands are especially vibrant during these seasons.
What are some things to do near Chiltern Hills?
You can explore nature trails through ancient beech woodlands, visit historic market towns, or enjoy outdoor activities such as cycling and horse riding. The region also has traditional pubs, local craft shops, and wildlife reserves that highlight its rural character.
How is the weather near Chiltern Hills?
Chiltern Hills experiences cool winters, with temperatures around 34–47°F (1–8°C), and mild summers near 53–73°F (12–23°C). Rainfall is moderate throughout the year, so packing layers and a waterproof jacket is often suggested for outdoor plans.
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- The O2
- ExCeL London
- Tower Bridge
- Silverstone Circuit
- Emirates Stadium
- Tottenham Hotspur Stadium
- Cotswolds AONB
- Clapham Common
- University of Oxford
- Thorpe Park Resort
- Victoria Park
- The National Bowl
- Blenheim Palace
- Buckingham Palace
- Big Ben
- Alexandra Palace
- London Eye





