Holiday rentals near Chiltern Hills

We found 2,174 holiday rentals — enter your dates for availability
Select the perfect holiday home within close proximity to Chiltern Hills. Holiday homes provide the best amenities for you and your friends, family or even pets, such as parking and a hot tub. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chiltern Hills

Why visit Chiltern Hills

  • Scenic Countryside: Enjoy rolling hills, picturesque villages, and lush woodlands that offer a serene escape and perfect backdrop for leisurely walks and cycling.
  • Historic Charm: Discover charming churches and historic houses that echo the rich heritage of the region.
  • Cultural Experiences: Explore local museums and vintage cinema showcasing the unique cultural tapestry of Chiltern Hills.
  • Outdoor Adventures: Engage in a variety of outdoor activities amidst the enchanting natural beauty.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment ideal for families and nature enthusiasts alike.

Popular types of accommodation around Chiltern Hills

Welcome to Chiltern Hills, England, where scenic beauty meets historic charm. Dive into the best Chiltern accommodation, from cosy cottages and private holiday homes to stylish apartments. Explore local attractions and landmarks nestled within these rolling hills, whilst enjoying transparency, savings and reassurance in your holiday rental. Discover the perfect retreat, whether you're seeking holiday rentals in Chiltern Hills or nearby, and experience the unique allure of this quintessential English destination.

  • Apartments: The leading choice in Chiltern Hills, apartments offer stylish, modern living spaces ideal for an urban retreat.
  • Private Holiday Homes: These exclusive, self-contained homes provide a private and homely escape in the scenic countryside.
  • Cottages: Quaint cottages deliver a cosy, traditional experience, perfect for those seeking a charming rural break.
  • Chalets: Nestled in nature, chalets offer a comfortable, rustic setting with a touch of luxury.
  • Cabins: For a back-to-nature experience, cabins provide a simple, inviting retreat amid the countryside.**

Top attractions near Chiltern Hills

Chiltern Hills, England, United Kingdom, offers a delightful blend of history and natural beauty, perfect for adventure seekers and families alike. Explore historic houses, charming churches, and the captivating vintage cinema. Engage in outdoor activities and discover local museums that showcase the rich culture of the region. With friendly attractions and thrilling adventures, Chiltern Hills promises an enriching experience for every visitor.

  • Warner Bros. Studio Tour London: Discover the magic of film-making with engaging exhibits and behind-the-scenes insights, offering a delightful family experience near the picturesque Chiltern Hills.
  • Windsor Castle: Immerse yourself in regal splendour and romance, exploring centuries of history and culture in a majestic setting close to the scenic Chiltern Hills.
  • Cliveden House: Experience a rich tapestry of culture and heritage, with splendid architecture and captivating gardens, all within reach of the charming Chiltern Hills.

Things to do recommended for couples

Discover the enchanting Chiltern Hills, ideal for couples seeking romance. Wander hand-in-hand along picturesque trails, indulge in a cosy picnic at a scenic viewpoint, or enjoy a delightful wine tasting at a local vineyard. Experience the charm of quaint villages, perfect for a memorable getaway together.

Things to do recommended for families

Families exploring the Chiltern Hills can enjoy a delightful day at the Roald Dahl Museum and Story Centre, immersing in the world of the beloved author. Additionally, the stunning countryside offers numerous walking trails perfect for family picnics and adventures together.

Things to do recommended for groups

Groups visiting the Chiltern Hills can embark on an exhilarating adventure at Go Ape in Wendover Woods, located 13km away. Experience the thrill of ziplining and navigating treetop ropes courses amidst the beautiful outdoor scenery, perfect for bonding and creating lasting memories.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Chiltern Hills

Whether you're journeying with a group, travelling as a family, taking your pets along or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking suggestions for you.

  • Traveling to Chiltern Hills with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for a group get-together. Thankfully, you can narrow your search for all these options — and more — on Stayz.
  • Traveling to Chiltern Hills with young kids: Traveling with young children can present its challenges. You must prioritise their comfort and safety and ensure access to age-appropriate amenities, such as a private swimming pool. It is also advisable to consider your closeness to family-friendly attractions.
  • Taking your pets with you to Chiltern Hills: For many, a family getaway isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chiltern Hills: If you're in search of holiday rentals offering discounts for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chiltern Hills

Chiltern Hills offers an enchanting escape for travellers seeking a blend of relaxation and natural beauty. Explore the stunning landscapes adorned with rolling hills, picturesque villages, and lush woodlands. Enjoy leisurely walks and cycling routes that wind through the charming countryside, immersing yourself in the friendly atmosphere. With a variety of local attractions, you can truly experience the essence of the Chilterns, making it an ideal holiday destination for families and nature enthusiasts alike.

  • High Wycombe: Located approximately 6km from the Chiltern Hills, High Wycombe is a vibrant city known for its family-friendly atmosphere and rich cultural experiences. Visitors can enjoy a variety of activities, from the bustling shopping centres to the lively theatres that host a range of performances. The town is also close to significant local landmarks, including a prominent sports facility stadium and beautiful national parks, perfect for outdoor enthusiasts looking to explore the local scenery and wildlife.
  • Amersham: Amersham, situated around 11km from the Chiltern Hills, offers a delightful mix of outdoor pursuits and cultural attractions. The town is renowned for its picturesque streets and engaging theatre scene, making it an excellent destination for families. Visitors can explore a variety of shopping areas and entertainment venues, while the proximity to notable landmarks, such as a sports facility stadium and charming national parks, provides ample opportunities for outdoor enjoyment and exploration of the local heritage.
  • Marlow: Marlow is approximately 13km from the Chiltern Hills and is famed for its stunning scenery and adventurous spirit. Nestled along the River Thames, it provides a perfect setting for outdoor activities, including golf and leisurely walks along the riverbank. The town is dotted with recreational areas and shopping mall centres, offering a delightful blend of relaxation and retail therapy. Notable local attractions include historic places and houses, inviting visitors to delve into the area’s rich history while enjoying its natural beauty.

Booking with Stayz is a breeze

If you're aiming to cut costs on your upcoming journey, consider the benefits of flexible travel dates, as fares often fluctuate. You may also enjoy substantial savings by opting for a longer stay. To locate a Stayz property that aligns with your budget, simply use our filtering options to sort by price, location, and holiday rental type.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides you with a dedicated area to initiate new journeys, pick up where you left off, or examine and manage your bookings. Properties you have either saved or reserved are now categorised as Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best holiday rentals near Chiltern Hills?
The best holiday rentals near Chiltern Hills are typically located in charming villages and market towns throughout the area, offering easy access to the scenic landscapes. You will find a wide array of properties, from modern apartments in town centres to private holiday houses located in the countryside. These options provide excellent bases for exploring the natural beauty of the region. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties and experiencing more rural settings, ensuring you can find the best holiday rentals near Chiltern Hills.

Many of these holiday rentals come with practical amenities, such as laundry facilities for longer stays and options where pets are permitted, which is great for guests travelling with their furry companions. Properties with a desk are also available for those needing to work remotely. These homes are ideal for families, couples, or anyone seeking a peaceful escape in the English countryside.
Are there any cheap holiday rentals near Chiltern Hills?
There are several affordable holiday rentals near Chiltern Hills, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around £70 per night in areas like Aylesbury or High Wycombe, which are on the periphery of the Chilterns. Some stays even drop below £50 per night in November during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio apartments to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs like Henley-on-Thames or Marlow. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Chiltern Hills while keeping costs down, so you can have a comfortable stay.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Chiltern Hills?
There are over 250 pet-friendly holiday rentals near Chiltern Hills, making it an excellent destination for guests travelling with their animal companions. These properties, primarily private homes and apartments, are dotted throughout the charming towns and villages within the Chiltern Hills area. Many offer amenities specifically for pets, such as food and water bowls, and some even provide fenced yards or easy access to outdoor spaces, alongside essential comforts like fully equipped kitchens and Wi-Fi for guests.

When searching for the best pet-friendly holiday rentals near Chiltern Hills, it is always wise to review individual property rules regarding pet size restrictions or any additional fees. The Chiltern Hills themselves are very welcoming to pets, offering extensive open spaces and ample room to roam, superb for long walks.
What are the top holiday rentals with pools near Chiltern Hills?
There are approximately 15 holiday rentals near Chiltern Hills that feature swimming pools, offering both private and shared options. These properties primarily consist of apartments and private holiday houses, many of which provide either private backyard pools or access to shared community pools, including some indoor choices. Most of these homes are well-appointed with amenities such as full kitchens, Wi-Fi, and comfortable living areas, making them suitable for families and groups seeking a relaxing stay.

When selecting a rental, consider whether a private pool, offering seclusion, or a shared pool, which might include additional facilities like fitness centres, best suits your preferences. For cooler months, look for properties that offer heated or indoor pool options to ensure year-round enjoyment.
What are the best family holiday rentals near Chiltern Hills?
There are over 290 family-friendly holiday rentals, including numerous private homes and apartments, in the regions surrounding Chiltern Hills. These properties are designed to offer ample space for families, often featuring multiple bedrooms and bathrooms. Many come equipped with full kitchens, washer/dryers, and outdoor play areas such as gardens or patios, which are ideal for children. Some even provide entertainment options like books, video games, and designated play areas.

When selecting a home for your family stay, consider properties that offer distinct areas for adults and children to relax, and look for practical amenities like a fully equipped kitchen and laundry facilities to simplify your trip. Staying close to Chiltern Hills means less travel time and more opportunities to explore the beautiful surroundings.
Are there any luxury holiday rentals near Chiltern Hills?
Near Chiltern Hills, guests can find several luxury holiday rentals that offer natural scenery and modern comfort. These properties often feature private pools, deep soaking bathtubs, private chefs, and premium bedding. Many homes also provide amenities such as air conditioning, designer toiletries, and stunning mountain, lake, or river views.

These homes are ideal for families or larger groups, ensuring a comfortable stay with features like high-speed WiFi and spacious living areas. Many of these top-tier stays are managed by highly rated Stayz hosts, promising a professional and premium experience.
Where should I stay when visiting Chiltern Hills?
When visiting Chiltern Hills, there are several charming areas offering excellent holiday rental options. The market towns within the Chiltern Hills, such as Henley-on-Thames, provide a wonderful base with properties offering access to scenic riverside walks and local shops.

For those seeking a more rural experience, areas around Wendover or Princes Risborough offer secluded homes with direct access to hiking trails and the natural beauty of the Chiltern Hills. These properties are a short drive from the main attractions, allowing guests to enjoy the peaceful countryside.

Alternatively, villages like Great Missenden offer a blend of village life and countryside access. Here, you can find holiday rentals that provide a convenient starting point for exploring the wider Chiltern Hills area.
What is the cheapest month to stay near Chiltern Hills?
The cheapest time to find holiday rentals near Chiltern Hills is typically during the late Autumn (November) and Winter (January to February), excluding the Christmas and New Year's weeks. November is frequently the single cheapest month, often providing the best deals on homes and properties, with rates potentially 15-25% lower than peak summer prices. Guests can often find various savings and greater availability during these months.
Are there any lakefront holiday rentals near Chiltern Hills
Lakefront holiday rentals near Chiltern Hills offer a great mix of comfort, scenery, and outdoor adventure. Many are located along quiet lakes like those found in the nearby Cotswold Water Park or smaller lakes within a short drive. These properties are a short drive from Chiltern Hills, offering convenient access to water activities such as kayaking, fishing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy mountain and lake views, spot wildlife, and unwind in peaceful surroundings after exploring local trails.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas