Holiday rentals in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

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Top guest favourite
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 in Cuddington
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 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, 326 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 riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading
4.98 out of 5 average rating, 425 reviews

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Charming, riverside log cabin on the bank of the Kennett, overlooking a nature reserve. Privately located in my back garden there is a large open plan room with 2 double sofa beds, sleeping 4, a slate bed pool table & Hi Fi system. There's a luxury en suite bathroom with copper bathtub, shower, basin & WC. There are basic kitchen facilities with kettle, toaster, double hot plate, microwave & grill, sink & refrigerator/freezer. A veranda with 2 bbq's & seats plus lower deck overlook the river.

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 in Owlswick
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 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, 343 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.

Guest favourite
An airy living space is highlighted by high ceilings and natural light streaming through large windows. A mix of seating options, including a gray sofa and a white armchair, surrounds a coffee table. A dining area with white chairs complements a gray sideboard.
Cottage in Amersham
4.97 out of 5 average rating, 157 reviews

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.

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 in Radnage
5 out of 5 average rating, 226 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 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, 1,622 reviews

Romantic Oak Cabin Berkhamsted

This cosy luxurious self contained oak frame 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, this is perfect for outdoor lovers but equally suitable for a romantic night in. 1.5 miles down the road, the popular market town of Berkhamsted is offering atmospheric pubs and bars for a special treat out. The cabin offers comfortable, spacious living with King size bed.

Top 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 in Wendover
4.9 out of 5 average rating, 305 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. The surrounding area has some renowned country walks and cycle paths.

Top guest favourite
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 in Warfield
4.98 out of 5 average rating, 307 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 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, 481 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
The exterior of Cutter's Barn is highlighted, showcasing its stone and brick façade. Large windows invite natural light, while the surrounding countryside is visible. A gravel area leads to the entrance, with potted plants adding greenery. A bench offers a place to relax.
Cottage in Chilton
4.99 out of 5 average rating, 290 reviews

Cutter's Barn

A brick and Stone barn that sleeps 6, Cutter’s Barn has been recently refurbished to a very high standard and is set on a small livestock Farm in stunning rural Buckinghamshire. Magnificent views of rolling hills and valleys on the edge of the Chiltern Hills, but close to Oxford and excellent transport links to London. Cattle and Sheep share the surrounding pastures with abundant wild bird and animal life.

Popular amenities for Chiltern Hills holiday rentals