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Vacation rentals in Chiltern Hills

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Top-rated vacation rentals in Chiltern Hills

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Top guest favorite
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, 234 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 favorite
A well-maintained garden features a stone pathway leading to the cottage, bordered by green lawns and vibrant red flowers. Various outdoor seating options are scattered throughout the area, with potted plants adding a charming touch. A distant shed is visible, complementing the serene landscape.
Cottage
4.96 out of 5 average rating, 169 reviews

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.

Top guest favorite
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, 328 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.

Guest favorite
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, 101 reviews

Romantic cosy cottage near Oxford & The Cotswolds

Romantic cottage in the sleepy Oxfordshire village of Cuddesdon, close to Oxford, Le Manoir, 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 favorite
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, 222 reviews

17th Century Barn near Le Manoir aux Quat'Saisons

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 favorite
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
4.98 out of 5 average rating, 146 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 favorite
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
4.97 out of 5 average rating, 344 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 favorite
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.
Guesthouse
5 out of 5 average rating, 227 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 favorite
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, 349 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 favorite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage
4.98 out of 5 average rating, 309 reviews

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Top guest favorite
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
4.96 out of 5 average rating, 482 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 favorite
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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