Holiday houses in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

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Top Guest favourite
A wooden exterior with smooth, light brown cladding is featured, with a small outdoor seating area containing two white chairs. A charming flower arrangement sits on the table, and a rustic wooden gate leads to a lush green landscape in the background.
Home in Stoke Talmage
4.97 out of 5 average rating, 238 reviews

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.

Top Guest favourite
The spacious open-plan living room features large windows framing views of the surrounding greenery. A comfortable seating arrangement includes two sofas and a central coffee table. A decorative ladder leads to the mezzanine, which accommodates a King size bed. Soft lighting enhances the cabin's inviting feel.
Cabin in Potten End
4.96 out of 5 average rating, 1,647 reviews

Romantic Oak Cabin Berkhamsted

This cosy luxurious self contained oak framed cabin offers the perfect peaceful setting for a relaxing getaway. Listen out and you may hear the owls at night. Backing onto the National Trust Ashridge Forest, perfect for outdoor lovers yet equally suitable for a romantic night in. 1.5 miles away, the popular market town of Berkhamsted, offering atmospheric pubs and bars for a special night out. The cabin offers cozy spacious living with King size bed on a mezzanine floor! STRICT NO PET POLICY!

Top Guest favourite
The bright living area features vaulted ceilings with original wooden beams and skylights. A comfortable sofa sits beside a soft ottoman, while a white coffee table holds decorative items. Large glass doors lead to an outdoor space, and a wall-mounted TV is positioned for viewing.
Barn in Buckinghamshire
4.97 out of 5 average rating, 333 reviews

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.

Top Guest favourite
A modern kitchen is displayed, featuring light grey cabinetry and wooden countertops. An induction oven and cooking utensils are visible. A dining table with two benches is positioned near the window, and a washing machine stands adjacent to the cabinetry. Solid oak flooring enhances the space.
Tiny home in Cuddington
4.99 out of 5 average rating, 103 reviews

Modern Self-Contained Detached Studio in Village

The Studio is a modern, self-contained and stylish space with king sized bed and fully fitted kitchen. Detached space with secure WiFi, off-road sheltered parking & private entrance, perfect for self-catered stays and business trips. Situated in a picturesque village backing onto open fields and a short walk from The Crown pub. Just 2 miles from Haddenham & Thame train station (direct links to Oxford & London), 15 minutes from M40 motorway & 4 miles north of Thame. Not suitable for infants.

Top Guest favourite
The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn in Great Milton
4.96 out of 5 average rating, 224 reviews

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.

Top Guest favourite
The exterior of the studio is shown, featuring a charming brick facade surrounded by greenery. Double French doors open into the interior, accompanied by a small patio area with decorative chairs. The setting includes a well-maintained garden leading to a serene atmosphere.
Guesthouse in Owlswick
4.98 out of 5 average rating, 148 reviews

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.

Top Guest favourite
A charming cottage is set in a green landscape, featuring a sloped roof and dark exterior walls. The front porch is accessible by steps and showcases a small seating area with a table and chairs. Large windows allow natural light to brighten the entrance.
Barn in Berkhamsted
4.98 out of 5 average rating, 385 reviews

The Stables in Historic Berkhamsted

Welcome to one of the most historic parts of Berkhamsted - the hilltop site of Old Berkhamsted Place, and the original Grade 2* listed barn which remains, reputedly, the largest medieval barn in the counties of Beds, Bucks & Herts. The Stables is a spotlessly chic cottage for 2 with large gardens & parking, offering luxury linen & towels, wi-fi & TV. Ideal town/country position - 10mins walk to town centre with cafes, restos, boutiques and antique stores, and train to London is only 35mins!

Top Guest favourite
The exterior of Chiltern Barn is depicted, showcasing a two-story building with a slate roof and natural stone façade. Large glass doors open onto a stone patio area, and a cobbled courtyard is visible in front, framed by lush greenery and a clear blue sky.
Cottage in High Wycombe
4.97 out of 5 average rating, 348 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

Top Guest favourite
The exterior of The Dairy is shown, featuring a charming brick facade with large windows. A wooden deck provides outdoor seating space, surrounded by lush green lawns and trees. The peaceful countryside surrounds the property, inviting relaxation in a natural setting.
Farm stay in Aylesbury
5 out of 5 average rating, 154 reviews

Countryside Getaway - Luxurious Converted Dairy

The Dairy is a beautifully converted luxury 2 bedroom property located on Middle Farm in the Buckinghamshire countryside. An idyllic setting perfect for a peaceful retreat with everything you will need! A bright open plan kitchen/dining/living room with smart TV, large garden with patio and outdoor seating, 2 stunning bedrooms with large comfortable beds, and bathroom with power shower and bath. Host My House manages this property which is owned by Lesley & Terry Rose (who live on-site).

Top Guest favourite
The charming brick exterior of the barn features a slate roof and arched windows. A gravel driveway leads to the entrance, flanked by decorative plants. Two seating areas are positioned outside, inviting relaxation in a serene garden setting.
Guesthouse in Worminghall
4.92 out of 5 average rating, 203 reviews

Charming barn conversion with vast living space

Set alongside our beloved family home, in 7 acres of open farmland, this wonderful space offers a welcome retreat from the stresses of everyday life. Worminghall is predominantly a farming village, within easy vehicular access to Oxford and the market town of Thame. Situated on the Oxfordshire/Buckinghamshire borders, it's the perfect location if you are visiting for a wedding or function nearby, or simply wish to explore the area's many local attractions.

Top Guest favourite
The open plan living area features a spacious gray sofa adorned with colorful cushions, positioned around a glass coffee table. Large glass doors allow natural light to flood the space, with views of the garden. A plush ottoman and a media unit complement the inviting atmosphere.
Barn in Shabbington
4.96 out of 5 average rating, 491 reviews

A delightful barn conversion

Set in the gardens of our 17th Century house, we are offering you a well designed barn conversion which is spacious and light. We are situated in the pretty rural village of Shabbington, just outside the market town of Thame, and surrounded by the Oxfordshire/Buckinghamshire countryside. We are ideally placed for those wishing to visit local attractions such as Bicester Village, Oxford, Waddesdon Manor and Blenheim Palace.

Top Guest favourite
Townhouse in Buckinghamshire
4.96 out of 5 average rating, 183 reviews

Princes Risborough, 3 Double Bedrooms, Big Garden

This is our lovely end-terraced Edwardian house where you can enjoy country walks in the Chilterns, go for bike rides, or have a BBQ in the beautiful garden. The house is just a short walk from the train station in the medieval market town of Princes Risborough. We have private parking for one car and bicycles are available for the guests to use. The house is ideal for max 4 grown-ups, your pet can be brought on request.

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