
Holiday rentals 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.

A peaceful rural retreat
"A recently refurbished self-contained annex in the midst of beautiful Oxfordshire countryside. Close to the Chilterns, the pretty market towns of Thame and Watlington and just 20 minutes drive from Oxford. There are excellent walks and numerous pubs and restaurants with delicious food and warm fires. The property is a separate annex from the main house and is perfect for a relaxing break. It has a sitting area and kitchen, a bedroom with beautiful views, a superking bed and a modern bathroom.

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.

Luxury Oxfordshire Cottage | Dogs | Pub
Escape to a stylish, cosy cottage near Oxford, inspired by The Holiday. Perfect for couples or friends, it offers peaceful countryside views, king-size beds and a log fire for relaxing evenings. Dog-friendly and just a short stroll to the award-winning Bat & Ball pub, it’s an ideal base for exploring Oxford, Blenheim Palace and the Cotswolds. Perfect for summer escapes near Oxford - enjoy long lunches in the enclosed garden, countryside walks and evenings at the pub. Few remaining June dates.

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.

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.

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.

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.

Delightful, rural, modern cottage, large garden.
Spectacular , quiet, rural cottage. This cottage contains a large maisonette room with a super-king bed and a downstairs room with two double beds, ideal for up to 4 children who can share or two adults who prefer double beds. The bathroom has a bath with a shower in it. There is a fully operating kitchen/dining room. Lots of walks nearby either to the pubs in Little Missenden, Penn woods and Penn Street or further into Old Amersham. Shared use of a large garden and tennis court.

Countryside Retreat with hot tub
This modern country retreat features panoramic views of the Oxfordshire countryside from the open-plan kitchen, living room. Ideal for a peaceful getaway, our home offers high-speed Wi-Fi, a fully equipped kitchen, and cozy furnishings. Two bedrooms featuring superking beds, one with ensuite. Outside bbq area with comfy seating, firepit, dining area and hot tub. Whether you're here for a weekend escape or a longer stay, this house provides the perfect setting to relax and unwind.

Luxury self-contained Annexe with balcony Jacuzzi
Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.

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.
Popular amenities for Chiltern Hills holiday rentals
Other great holiday rentals in Chiltern Hills

The Potting Shed - boutique countryside hideout

Honey Barn - Stunning 4-Bed Rural Paradise

Straw Plaiters Cottage

The Old Raj, Wendover

Stunning Apartment in the Conservation Area.

Kop Hill Barn in the heart of the Chilterns

Spacious, Self Contained Annexe with Parking

Deluxe Lodge for Couples & Business Travellers.
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
- Cotswolds AONB
- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- Kings Cross
- The O2
- Wembley Stadium
- Buckingham Palace
- Marble Arch
- Tottenham Court Road
- Tower Bridge
- London Bridge
- Big Ben
- Trafalgar Square
- Emirates Stadium
- ExCeL London
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common





