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Holiday rentals in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest house 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

9–16 Jun

₹5,617 per night

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.

21–28 Mar

₹14,080 per night

Guest favourite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 233 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.

26 Feb – 5 Mar

₹17,424 per night

Guest favourite

Guest house 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.

19–26 Nov

₹13,297 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.

29 Mar – 5 Apr

₹10,380 per night

Guest favourite

Guest suite in Towersey

4.96 out of 5 average rating, 354 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

7–14 Oct

₹8,461 per night

Guest favourite

Tiny home in Aylesbury

4.98 out of 5 average rating, 153 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 Sep – 6 Oct

₹27,953 per night

Guest favourite

Home in Tetsworth

5.0 out of 5 average rating, 243 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, hot tub & loungers.

8–15 Oct

₹20,035 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.

2–9 Oct

₹15,246 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.

13–20 Jul

₹8,325 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!

2–9 Nov

₹13,598 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.

9–16 Jan

₹8,671 per night

Holiday rentals for every style

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Popular amenities for Chiltern Hills holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Chiltern Hills

Guest favourite

Cabin in Long Crendon

4.97 out of 5 average rating, 238 reviews

Stylish, airy Scandinavian-style summerhouse

28 Oct – 4 Nov

₹11,814 per night

Guest favourite

Guest house in Radnage

4.99 out of 5 average rating, 167 reviews

Chilterns Country Escape

27 Sep – 4 Oct

₹19,243 per night

Guest favourite

Cottage in High Wycombe

4.97 out of 5 average rating, 245 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

19–26 May

₹12,768 per night

Guest favourite

Guest house in Buckinghamshire

4.98 out of 5 average rating, 219 reviews

The Barn at The Grove

11–18 Jul

₹10,251 per night

Guest favourite

Barn in Great Milton

4.95 out of 5 average rating, 139 reviews

17th Century Barn near Le Manoir aux Quat’Saisons

26 Jul – 2 Aug

₹30,269 per night

Guest favourite

Home in Stoke Talmage, Thame

4.97 out of 5 average rating, 103 reviews

A peaceful rural retreat

9–16 Sep

₹8,565 per night

Shepherd’s hut in Oxfordshire

4.78 out of 5 average rating, 172 reviews

Cosy Woodland Cabin Escape ~ Long Stays Available

5–12 Mar

₹9,385 per night

Guest favourite

Bungalow in Wendover

4.96 out of 5 average rating, 117 reviews

The Lodge - Self Contained Bungalow Wendover

20–27 Dec

₹12,165 per night

Destinations to explore