Holiday rentals in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

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Guest favourite
A private courtyard features a small round table and two chairs, surrounded by gravel. Potted plants add greenery, and a wooden fence provides an unobstructed view of the expansive fields beyond. A decorative lattice offers partial privacy while enhancing the outdoor ambiance.
Casa particular
4.9 out of 5 average rating, 309 reviews

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.

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
4.97 out of 5 average rating, 240 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 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
4.97 out of 5 average rating, 335 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
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
4.96 out of 5 average rating, 225 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.
Guest house
4.98 out of 5 average rating, 149 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
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!

Guest favourite
A cozy bedroom corner is showcased with a spacious bed dressed in crisp linens and soft pillows. A bedside table holds a decorative tray with small items, a lamp provides warm light, and a stylish vase features greenery against the softly painted wall.
Cottage
4.96 out of 5 average rating, 109 reviews

Romantic cosy cottage near Oxford & The Cotswolds

Romantic cottage in the sleepy Oxfordshire village of Cuddesdon, close to Oxford, The Cotswolds, Henley, Blenheim Palace and quick links to London. Reminiscent of the cottage from ‘The Holiday’, its warm, calm, cosy interiors make it perfect for couples, friends or families looking for a relaxing break away. Cosy up by the fire, daydream whilst looking over the beautiful countryside views, linger in the cosy king size beds, or stroll up to The Bat and Ball for an amazing dinner.

Top guest favourite
A charming wooden annexe is shown with a sloped roof and multiple large windows. Lush greenery surrounds the property, and a well-maintained picket fence is adorned with flower boxes. Visible are outdoor steps leading to a top floor entrance amid a gravel pathway.
Guest house
5 out of 5 average rating, 229 reviews

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.

Top guest favourite
The exterior of the modern annexe is showcased, featuring large glass doors that allow natural light to fill the interior. A spacious balcony is visible above, bordered by glass, and wooden furniture is arranged on the terrace, ideal for outdoor relaxation.
Home
5 out of 5 average rating, 356 reviews

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.

Top guest favourite
The exterior of the lodge is shown, featuring wooden walls and a slate roof. A private courtyard is visible, bordered by greenery and a stone-paved area. Large windows allow natural light to enter the lodge, creating an inviting atmosphere.
Tiny home
4.97 out of 5 average rating, 220 reviews

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.

Top guest favourite
A contemporary studio apartment is positioned along the riverbank, featuring a modern design with large glass windows. A graceful weeping willow tree frames the scene, adding a natural element to the tranquil waterfront setting. Gentle ripples are visible on the water's surface.
Loft
4.94 out of 5 average rating, 208 reviews

Luxury Boathouse Apartment - central Henley

The Boathouse is a completely private studio apartment with wonderful river views. Furnished to a high standard with luxury bed linens and towels, and fully equipped with everything you could need. The perfect location for the Henley Royal Regatta, Henley Festival and The Rewind Festival Relaxing location that is perfect for watching the world and river go by, but also close enough to the hustle and bustle of the town and it's many restaurants and cafes.

Top guest favourite
Townhouse
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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