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Holiday rentals in Chiltern Hills

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Top-rated holiday rentals in Chiltern Hills

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Guest house in Bennett End

4.87 out of 5 average rating, 405 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

7–14 Aug

$108 SGD per night

Guest favourite

Barn in Buckinghamshire

4.96 out of 5 average rating, 217 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.

27 Apr – 4 May

$226 SGD per night

Guest favourite

Barn in Great Milton

4.95 out of 5 average rating, 142 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.

5–12 Sep

$514 SGD per night

Guest favourite

Shepherd’s hut in Ewelme

4.99 out of 5 average rating, 360 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.

24–31 Mar

$172 SGD per night

Guest favourite

Cottage in High Wycombe

4.97 out of 5 average rating, 245 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.

19–26 May

$195 SGD per night

Guest favourite

Guest house in Oxfordshire

4.97 out of 5 average rating, 349 reviews

Stunning country retreat/romantic mini break

A country hideout 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.

31 Mar – 7 Apr

$223 SGD 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

26 Aug – 2 Sep

$142 SGD per night

Guest favourite

Tiny home in Aylesbury

4.97 out of 5 average rating, 158 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.

23–30 Dec

$532 SGD per night

Guest favourite

Guest house in Radnage

4.99 out of 5 average rating, 169 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.

15–22 Dec

$323 SGD per night

Guest favourite

Cabin in Potten End

4.96 out of 5 average rating, 1352 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.

30 Sep – 7 Oct

$256 SGD per night

Guest favourite

Casa particular in Wendover, Buckinghamshire

4.89 out of 5 average rating, 227 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.

26 Jul – 2 Aug

$140 SGD 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!

4–11 Dec

$228 SGD per night

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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

Home in Tetsworth

5.0 out of 5 average rating, 244 reviews

Luxury self-contained Annexe with balcony Jacuzzi

7–14 Sep

$341 SGD per night

Guest favourite

Cottage in Saunderton

4.95 out of 5 average rating, 132 reviews

Idyllic escape - wild swimming, stunning walking

14–21 Jul

$238 SGD per night

Guest favourite

Cabin in Long Crendon

4.97 out of 5 average rating, 239 reviews

Stylish, airy Scandinavian-style summerhouse

28 Aug – 4 Sep

$198 SGD per night

Guest favourite

Townhouse in Buckinghamshire

4.97 out of 5 average rating, 132 reviews

Princes Risborough, 3 Double Bedrooms, Big Garden

28 Jan – 4 Feb

$226 SGD per night

Guest favourite

Home in Stoke Talmage, Thame

4.97 out of 5 average rating, 107 reviews

A peaceful rural retreat

20–27 Aug

$135 SGD per night

Guest favourite

Loft in Aylesbury

4.93 out of 5 average rating, 258 reviews

Timber loft studio flat - private and cosy

8–15 Jun

$114 SGD per night

Shepherd’s hut in Oxfordshire

4.79 out of 5 average rating, 174 reviews

Cosy Woodland Cabin Escape ~ Long Stays Available

15–22 Oct

$151 SGD 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

18–25 Oct

$291 SGD per night

Destinations to explore