Holiday houses in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

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Guest favourite

Barn in Buckinghamshire

4.96 out of 5 average rating, 216 reviews

Beautiful cosy Dinky 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.

13–20 Nov

$295 NZD per night

Guest favourite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 234 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

30 Jan – 6 Feb

$360 NZD per night

Guest favourite

Guesthouse in Oxfordshire

4.97 out of 5 average rating, 344 reviews

Stunning country retreat/romantic mini break

A stunning conversion above our detached oak framed barn. Stylishly furnished in a rustic luxury theme ensuring this little retreat ticks all boxes to make your stay comfortable & cosy! Extremely spacious and an ideal place to come and relax for a romantic countryside break. There are two great pubs within walking distance which offer amazing food although there is a very well equipped kitchen should you like to cook for yourselves. Easy access to Oxfordshire best countryside walks too.

15–22 Jan

$271 NZD per night

Guest favourite

Cottage in Sarratt

5.0 out of 5 average rating, 187 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

26 Mar – 2 Apr

$354 NZD per night

Guest favourite

Shepherd’s hut in Ewelme

4.99 out of 5 average rating, 357 reviews

Luxury Shepherd's Hut with stunning sunset views!

Welcome to Honeysuckle, our luxury shepherd's hut with stunning views across the fields in the Chilterns. In the evenings sit and watch the sun go down around your fire pit or stay cosy indoors with your log burner. We are a working farm and you may see the tractor trundle past feeding our herds of Texal sheep or Limousin cows grazing in front of you, or watch the birds following the plough up and down. You have your own secluded, fenced and private garden area with seating and wildflowers.

23–30 Nov

$210 NZD per night

Guest favourite

Guest suite in Towersey

4.96 out of 5 average rating, 355 reviews

Peaceful village location with own entrance

The Annex is a delightful, warm, quiet and comfortable dwelling built within the garden of our village home and adjacent to our garage. Towersey is one mile from the market town of Thame, and has an excellent village pub plus access to the Phoenix Trail cycle & footpath. The Annex has its own entrance with parking space, a double bedroom with king sized bed & tv, and sitting room with fridge, microwave, coffee machine, kettle, toaster, plus tv. There is a power shower over the bath

1–8 Oct

$172 NZD per night

Guest favourite

Tiny home in Aylesbury

4.97 out of 5 average rating, 155 reviews

The Woodland Retreat With 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.

29 Jan – 5 Feb

$647 NZD per night

Guest favourite

Guesthouse in Radnage

4.99 out of 5 average rating, 167 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.

5–12 Nov

$407 NZD per night

Guest favourite

Cabin in Potten End

4.96 out of 5 average rating, 1349 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.

22–29 Sep

$318 NZD per night

Guest favourite

Casa particular in Wendover, Buckinghamshire

4.89 out of 5 average rating, 226 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.

22–29 Jun

$179 NZD per night

Guest favourite

Cabin in Chinnor

4.95 out of 5 average rating, 118 reviews

Lakeside Cabin - Stunning Countryside Getaway

Tranquil waterside cabin located within the luscious gardens of Town Farm Cottage, Kingston Blount. Views of pasture parkland, the lake and a huge variety of wildlife/flowers. You're welcome to explore the garden and see the donkeys and sheep in the next door field. Being at the foot of the Chiltern Hills and close to The Oxfordshire Way and Ridgeway Path, this is the perfect base for exploring the surrounding countryside. 1 dog under 10kg and over 12 months welcome!

14–21 Mar

$277 NZD per night

Guest favourite

Barn in Kingsey

4.93 out of 5 average rating, 409 reviews

Self-contained barn conversion

The Farrow is a pretty self-contained annex within the grounds of Nettlebed Barn. Set in tranquil surroundings on the edge of the 12th century hamlet of Kingsey it has the additional benefit of stunning picturesque views of rolling fields framed by the beautiful vista of the Chiltern hills . Just a 5 minute drive to Haddenham train station will give you access to central London in 40 minutes and the beautiful and historic city of Oxford in just 29 mins.

12–19 Oct

$180 NZD per night