Holiday rentals and lettings in Chiltern Hills

Holiday rentals and lettings in Chiltern Hills

Start comparing over 235 rentals in Chiltern Hills and book at the best price!

Find Holiday Rentals & Lettings in Chiltern Hills

Highlights in Chiltern Hills

  • Walks
  • Vineyards
  • View point
  • Family-friendly activities
  • National trust estate

Best Holiday Rentals & Lettings in Chiltern Hills

Guests agree: these stays are highly rated for location, cleanliness, and more.
Holiday Rental for 4 People in Medmenham, Buckinghamshire
Holiday Rental for 4 People in Medmenham, Buckinghamshire, Photo 1
Holiday Rental for 4 People in Medmenham, Buckinghamshire, Photo 2
Holiday Rental for 4 People in Medmenham, Buckinghamshire, Photo 3
Holiday Rental for 4 People in Medmenham, Buckinghamshire, Photo 4
more...
Medmenham, Buckinghamshire
Holiday Rental • 4 Guests • 2 Bedrooms
10.0
(4 reviews)
Step back in time without sacrificing comfort in this beautifully restored 17th-century Grade II listed cottage, nestled in the idyllic village of Medmenham — perfectly situated between Marlow-on-Thames and Henley-on-Thames (just 3 miles from each). Surrounded by the rolling hills of the Chilterns Area of Outstanding Natural Beauty, this lovingly renovated retreat blends centuries-old character with high-end modern touches, offering peace, romance and style in equal measure. 🏡 The Space Grade II listed 17th-century cottage with exposed oak beams and log-burner fireplace Sleeps 4 (2 double ...
from £183 / night
Holiday Letting for 4 People in Wallingford, Oxfordshire
Holiday Letting for 4 People in Wallingford, Oxfordshire, Photo 1
Holiday Letting for 4 People in Wallingford, Oxfordshire, Photo 2
Holiday Letting for 4 People in Wallingford, Oxfordshire, Photo 3
Holiday Letting for 4 People in Wallingford, Oxfordshire, Photo 4
more...
Wallingford, Oxfordshire
Holiday Letting • 4 Guests • 1 Bedroom
8.3
(7 reviews)
This cosy apartment is the perfect place to relax and unwind. Whether you’re here for work or leisure, Wallingford offers plenty to see and do — from historic sites and river walks to charming shops and pubs. 🏡 The Space Kitchen – Equipped with fridge, freezer, hob, oven, kettle, and microwave Living Area – A relaxing space with television and internet access Bedroom – One double bed with fresh linen provided Bathroom – Walk-in shower, toilet, and sink ✨ Additional Amenities Fresh linen and towels included On-site parking available 🌟 Local Recommendations Wallingford Castle Ruins (10 mins...
from £55 / night
Holiday Rental for 5 People in High Wycombe, Buckinghamshire
Holiday Rental for 5 People in High Wycombe, Buckinghamshire, Photo 1
Holiday Rental for 5 People in High Wycombe, Buckinghamshire, Photo 2
Holiday Rental for 5 People in High Wycombe, Buckinghamshire, Photo 3
Holiday Rental for 5 People in High Wycombe, Buckinghamshire, Photo 4
more...
High Wycombe, Buckinghamshire
Holiday Rental • 5 Guests • 2 Bedrooms
7.2
(27 reviews)
Welcome to our beautiful house in High Wycombe. We hope you enjoy your stay! We have personally thought through all of the amenities and hope to provide you with all the comforts of home. The surrounding area has a lot to offer and is sure to make your holiday one of a kind. Hellfire cave is 7 minute drive, Gym two minute walk, all amenities , Waitrose is walking distance. Pterol pumps two minutes drive As a self-catering house, you'll find everything you need for a perfect stay. The kitchen has a fridge, a hob, an oven, a kettle, a freezer and a microwave. The house is a perfect place to r...
from £117 / night

Other holiday ideas and property types in Chiltern Hills that might be interesting

Prices and availability

Current Holiday letting prices Chiltern Hills

£214for 11 Oct - 18 Oct
£234 annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Average price per week

Current holiday letting availability Chiltern Hills

43%for 11 Oct - 18 Oct
56% annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Percentage of available lettings

Holiday rentals and lettings in Chiltern Hills

A breathtaking holiday in the countryside

Formed by an outcrop of chalk, Chiltern Hills is an Area of Outstanding Beauty just a stone’s throw from West London. The 660 square mile conservation area offers a quick and perfect escape away from the city bustle. Come here to enjoy spectacular landscapes, scenic views, walking and cycling trails, wildlife spotting, and an array of outdoor activities. The area is dotted with charming villages and market towns filled with shops, pubs, and eateries worth stopping by. Chiltern Hills is a must-visit for families, couples, and nature lovers seeking a breath of fresh air and a break from the city.

A holiday rental in the green rolling hills

Treat yourself to a relaxing holiday in the green, verdant Chiltern Hills. There are countless holiday rentals scattered throughout the Chiltern Hills area in a wide range of sizes, styles, and locations, with a little something for every type of traveller. Families and large groups can opt for an oversized rental, with some accommodations designed to comfortably sleep up to 15 people! There are cosy, intimate rentals for couples to enjoy together. Opt for a rental with a garden surrounded by trees where you can enjoy plenty of privacy. Stay in a rental in one of the quaint villages or towns of Chiltern Hills where you can enjoy shops and restaurants within walking distance. Pet-friendly rentals are available if you’d like to bring your furry friend along! With so many excellent holiday rental options in Chiltern Hills, you’ll be sure to find one suited to your preferences.

Holidays in Chiltern Hills

The area and getting around

Arriving in Chiltern Hills

Chiltern Hills spans quite a large region and there are many ways to reach the various towns, villages, and points of interest throughout the area. The most popular ways to reach Chiltern Hills are by train, bus, or private car. Trains depart from London and arrive in various towns around Chiltern Hills. Hiring a car and driving yourself, however, offers the most freedom and flexibility to explore the area throughout your holiday.

Getting around Chiltern Hills

Since Chiltern Hills is a large area with a lot to see and do, the most recommended way of getting around is via private car. It is highly recommended to hire a car in London and to drive yourself to Chiltern Hills. If you prefer not to drive, you can use the train to reach Chiltern Hills and then use taxis or buses to get around for the duration of your holiday.

Travellers and activities

Chiltern Hills for families

Chiltern Hills is a wonderful destination for families to spend some time outdoors together. Let kids play and bounce around at Rush UK Trampoline Park in Wycombe. The massive jump area is safe enough for kids to jump and play alone while adults relax with some food from the café. Stop by to meet the cheetahs, lions, hippos and more at the popular ZSL Whipsnade Zoo near Dunstable where you can spend a leisurely afternoon strolling around the different sections of the zoo. You’ll find an aquarium, a butterfly house, a play park, and some restaurants.

Chiltern Hills for couples

Enjoy a romantic and scenic walk with your better half via the 3.5 mile loop from Chenies to Sarratt. This lovely walk passes through villages, farms, valleys, rivers, and a footbridge. Afterwards, pick up some farm fresh treats from Peterley Manor Farm shop where you’ll find top-quality produce and homemade items such as eggs, bread, pastries, vegetables, and more all at a reasonable price.

The Chiltern Hills stretch for 70 miles through Oxfordshire, Buckinghamshire, Hertfordshire, and Bedfordshire.

Top 5 travel tips in Chiltern Hills

1. Enjoy peaceful nature walks

Chiltern Hills is an excellent place for walkers with countless trails winding through valleys, woodlands, and along rivers. For a relatively easy but long walk through the area, try the 10-mile walk which goes from Rickmansworth to Chesham. This walk follows along a stream and leads through several charming villages, and you’ll see plenty of wildlife along the way. For shorter nature walks, visit Wendover Woods which boasts over 800 acres of trails, a play park for kids, a tree top adventure course, and a nice café.

2. Stop by the vineyards to sample local wines

If you’re a wine lover, hop around the various wineries in Chiltern Hills. The lovely views and the professional vineyard tour at Oaken Grove Vineyard is a must, and you’ll be able to sample a variety of high-quality wines here under the guidance of a knowledgeable staff member. Chiltern Valley Winery & Brewery is another must-visit with its picturesque vineyards and ambient tasting room where you can sample English wines, liqueurs, and beers!

3. Go to the highest viewpoint in Chiltern Hills

Coombe Hill is the highest point in Chiltern Hills at 852 feet above sea level. From the monument at the top of the hill, you can admire the panoramic views which stretch as far as the eye can see. This is a great place for a leisurely walk or to relax on the benches with a view.

4. Explore England’s smallest town

Situated in the heart of the Chiltern Hills is Watlington, England’s smallest town which bursts with charm and character. Walk the lovely streets of the town, pop into the cafés and shops, and visit the many green parks. It’s a lovely town to enjoy a peaceful few hours.

5. Tour the Hughenden National Trust manor

The remarkable Hughenden manor is an 18th-century Victorian mansion and one of the crown jewels of the Chiltern Hills. Here visitors can stroll around the lovely gardens and woodland paths surrounding the manor. You can tour the inside of the rooms of the house which display a collection of artefacts as you learn interesting stories about the former Prime Minister who used to inhabit the manor. Stop by the café where you can enjoy some delicious hot food items, cake, and coffee.

Information about holiday lettings in Chiltern Hills

🏡 Holiday lettings available: 240 properties.
💳 Discount available: up to -46%.
🌙 Minimum price per night: from £26.
⭐ Most popular amenities: Wi-Fi, garden and balcony.
🐾 Pet-friendly: 55 properties.
📶 For workation: 97% of the properties.
👩‍👩‍👧‍👦 For families: 8% of the properties.

FAQs: Holiday Rentals & Lettings in Chiltern Hills

Which facilities can you expect to find at the holiday lettings in Chiltern Hills?

Out of all the amenities available on Holidu, it appears that the holiday lettings in Chiltern Hills contain everything that travellers desire! Here, holiday lettings generally offer a variety of facilities, the most popular being: Wi-Fi (93%), garden (53%), and balcony (24%)... Not bad, right?

How are the holiday lettings rated in Chiltern Hills?

On average, the holiday lettings are quite highly rated. According to Holidu, 24% of holiday lettings have a rating of 4.5 stars. This is a fairly high ratio which allows us to confirm that you will without a doubt find the ideal holiday letting for a wonderful holiday!

Are the holiday lettings in Chiltern Hills child-friendly?

According to information from last year, 13% of holiday lettings in Chiltern Hills are child-friendly, it will therefore not be difficult to find the perfect holiday letting for you and your family.

Are the holiday lettings in Chiltern Hills pet-friendly?

According to Holidu's information, less than 10% of holiday lettings in Chiltern Hills accept pets. We can therefore assume that there are better destinations in the United Kingdom to take your faithful companion with you.

Do the holiday lettings in Chiltern Hills often have Wi-Fi?

Of course! According to the data collected last year, 93% of holiday lettings in Chiltern Hills have Wi-Fi. This means that you will be able to stay connected during your stay!

How much does it usually cost for holiday lettings in Chiltern Hills?

A big percentage of holiday lettings in Chiltern Hills (81%) cost less than £100 a night. Therefore, this destination is perfect for finding a cheap holiday letting!

Do the holiday lettings in Chiltern Hills often have a swimming pool?

Not always. According to Holidu's data, most of the holiday lettings in Chiltern Hills are not equipped with one.

Are the holiday lettings in Chiltern Hills suitable for trips in big groups or rather for an escape as a small group?

According to the information collected last year, 75% of holiday lettings are made for up to four people. Approximately 71% of the holiday lettings here have at least two separate bedrooms. Chiltern Hills is the perfect destination for taking your little family on holiday!

Do the holiday lettings in Chiltern Hills have a beautiful view?

24% of holiday lettings have a balcony or terrace, and 0% have a view. However, this does not represent the majority of properties here, so availability can be limited. If this is a priority for you, you should anticipate a bit more time for research. Also, don't forget to use the filters that suit you the best to be sure to find the holiday letting that is perfect for you. However, 53% of holiday lettings in Chiltern Hills have gardens, where you can enjoy the outdoors. If you like to have lunch or dinner outside, and especially if you like barbecues, 22% of the holiday lettings have them.

When it is best to travel to Chiltern Hills?

The facilities found in the properties in Chiltern Hills demonstrate that it is a holiday destination that can adapt to all tastes and times of the year. This is because there is a wide range of properties and services. Therefore, you will be able to enjoy Chiltern Hills when you feel like it.