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Vacation rentals in Chiltern Hills

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Top-rated vacation rentals in Chiltern Hills

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Guesthouse in Bennett End

4.87 out of 5 average rating, 403 reviews

Mary's Cabin

Completely peaceful, with fantastic views-totally isolated with its own private entrance. Set in the Chiltern hills- Mary’s Cabin is 2minutes stroll from the Restaurant of the Year- In an Area of Outstanding Natural Beauty;-walking, road & mountain biking- pub 7minutes up through the woods- 35mins from Heathrow and Oxford -Central London-50mins . Couples, solo adventurers, and small families (with 1small child). Sadly, since the advent of Covid, we no longer provide breakfast for our guests

Aug 29 – Sep 5

R1,464 ZAR per night

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.

Sep 5 – 12

R3,187 ZAR per night

Guesthouse in Oxfordshire

4.98 out of 5 average rating, 343 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.

Oct 29 – Nov 5

R3,056 ZAR per night

Shepherd’s hut in Ewelme

4.99 out of 5 average rating, 355 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.

Oct 21 – 28

R2,365 ZAR per night

Guest suite in Towersey

4.96 out of 5 average rating, 352 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

Oct 2 – 9

R1,945 ZAR per night

Tiny home in Aylesbury

4.98 out of 5 average rating, 151 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.

Jan 23 – 30

R7,292 ZAR per night

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.

Nov 3 – 10

R4,422 ZAR per night

Cabin in Potten End

4.96 out of 5 average rating, 1346 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.

Sep 1 – 8

R3,504 ZAR per night

Casa particular in Wendover, Buckinghamshire

4.89 out of 5 average rating, 224 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.

Jul 8 – 15

R1,913 ZAR per night

Cabin in Chinnor

4.95 out of 5 average rating, 117 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!

Oct 19 – 26

R3,125 ZAR per night

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.

Oct 13 – 20

R1,977 ZAR per night

Guesthouse in Buckinghamshire

4.98 out of 5 average rating, 219 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

Jul 10 – 17

R2,373 ZAR per night

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Popular amenities for Chiltern Hills vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Chiltern Hills

Home in Tetsworth

5.0 out of 5 average rating, 243 reviews

Luxury self-contained Annexe with balcony Jacuzzi

Oct 8 – 15

R4,570 ZAR per night

Cabin in Long Crendon

4.97 out of 5 average rating, 237 reviews

Stylish, airy Scandinavian-style summerhouse

Nov 25 – Dec 2

R2,715 ZAR per night

Barn in Great Milton

4.95 out of 5 average rating, 138 reviews

17th Century Barn near Le Manoir aux Quat’Saisons

Jun 2 – 9

R6,956 ZAR per night

Cottage in High Wycombe

4.97 out of 5 average rating, 245 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

May 25 – Jun 1

R3,125 ZAR per night

Home in Stoke Talmage, Thame

4.97 out of 5 average rating, 103 reviews

A peaceful rural retreat

Oct 9 – 16

R1,913 ZAR per night

Townhouse in Buckinghamshire

4.97 out of 5 average rating, 131 reviews

Princes Risborough, 3 Double Bedrooms, Big Garden

Mar 22 – 29

R3,427 ZAR per night

Apartment in Downley

4.86 out of 5 average rating, 118 reviews

The High Street Gallery,

Jan 26 – Feb 2

R2,010 ZAR per night

Guesthouse in Taplow

4.94 out of 5 average rating, 452 reviews

Luxury Rustic Log Cabin... secluded deck & garden

Apr 30 – May 7

R2,931 ZAR per night

Destinations to explore