Vacation rentals in Chiltern Hills

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Top-rated vacation rentals in Chiltern Hills

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

Superhost

Guesthouse in Bennett End

4.88 out of 5 average rating, 399 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

Feb 13 – 20

G$21,133 GYD per night
Guest favorite

Barn in Buckinghamshire

4.96 out of 5 average rating, 211 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 13 – 20

G$35,062 GYD per night
Guest favorite

Guesthouse in Oxfordshire

4.98 out of 5 average rating, 334 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.

Nov 26 – Dec 3

G$34,138 GYD per night

Popular amenities for Chiltern Hills vacation rentals

Other great vacation rentals in Chiltern Hills

Guest favorite

Cabin in Potten End

4.96 out of 5 average rating, 1333 reviews

Romantic Oak Cabin Berkhamsted

Sep 5 – 12

G$39,142 GYD per night
Guest favorite

Home in Tetsworth

5.0 out of 5 average rating, 238 reviews

Luxury self-contained Annexe with balcony Jacuzzi

Oct 1 – 8

G$48,722 GYD per night
Guest favorite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 228 reviews

A Unique Farm Retreat

Feb 7 – 14

G$44,736 GYD per night
Guest favorite

Bungalow in Wendover

4.96 out of 5 average rating, 115 reviews

The Lodge - Self Contained Bungalow Wendover

May 30 – Jun 6

G$27,482 GYD per night
Guest favorite

Barn in Great Milton

4.95 out of 5 average rating, 133 reviews

17th Century Barn near Le Manoir aux Quat’Saisons

Aug 15 – 22

G$77,713 GYD per night
Guest favorite

Cottage in High Wycombe

4.97 out of 5 average rating, 238 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

May 22 – 29

G$35,108 GYD per night
Guest favorite

Guesthouse in Buckinghamshire

4.98 out of 5 average rating, 218 reviews

The Barn at The Grove

Jun 10 – 17

G$25,659 GYD per night
Guest favorite

Guesthouse in Haddenham

4.99 out of 5 average rating, 150 reviews

Haddenham - detached annexe with parking

Jun 16 – 23

G$22,736 GYD per night
Guest favorite

Cottage in Cuddington

4.96 out of 5 average rating, 106 reviews

Escape to Country Living at its Finest!

Sep 2 – 9

G$50,412 GYD per night
Guest favorite

Guesthouse in Buckinghamshire

5.0 out of 5 average rating, 147 reviews

Red Kite Barn in a secluded valley close to Marlow

Apr 23 – 30

G$30,386 GYD per night
Guest favorite

Cottage in Buckinghamshire

4.97 out of 5 average rating, 283 reviews

Family friendly - rural, detached, home from home

Oct 27 – Nov 3

G$43,203 GYD per night
Guest favorite

Tiny home in Gloucestershire

4.94 out of 5 average rating, 186 reviews

Cotswolds Home, private lake, log burner, hot tub

Jan 3 – 10

G$112,295 GYD per night

Destinations to explore