Best Vacation Homes in Headley
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $357/Night
For 7 Nights US $2,497
398.26 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Breakfast
- Parking
US $102/Night
For 7 Nights US $714
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Internet
US $302/Night
For 7 Nights US $2,111
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Parking
- Air Conditioner
- Internet
US $143/Night
For 7 Nights US $999
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $259/Night
For 7 Nights US $1,811
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $152/Night
For 7 Nights US $1,061
370 ft²
3 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
US $285/Night
For 7 Nights US $1,996
Headley Luxury Rentals
18 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $2,811/Night
For 7 Nights US $19,676
538.2 ft²
15 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- View
- Parking
US $1,743/Night
For 7 Nights US $12,198
9999.67 ft²
18 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
Villa
- Hot Tub
- Balcony/Terrace
- View
US $1,661/Night
For 7 Nights US $11,628
US $623/Night
For 7 Nights US $4,362
2497.23 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Breakfast
- Kitchen
US $474/Night
For 7 Nights US $3,318
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Child Friendly
- Laundry
US $363/Night
For 7 Nights US $2,543
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Parking
- Internet
- Child Friendly
US $336/Night
For 7 Nights US $2,349
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Parking
- Internet
- Child Friendly
US $336/Night
For 7 Nights US $2,349
Headley Pet Friendly Vacation Rentals
237 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Pet Friendly
US $141/Night
For 7 Nights US $987
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- View
- Pet Friendly
US $175/Night
For 7 Nights US $1,227
10000 ft²
22 Guests
8 Bedrooms
8 Bathrooms
Family Friendly
House
- Pet Friendly
- Kitchen
- Laundry
US $1,343/Night
For 7 Nights US $9,401
6771 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,039/Night
For 7 Nights US $7,276
1 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pet Friendly
- Kitchen
- Laundry
US $382/Night
For 7 Nights US $2,674
818 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $304/Night
For 7 Nights US $2,127
807 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $277/Night
For 7 Nights US $1,936
Headley Large Vacation Homes
8999 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,964/Night
For 7 Nights US $13,748
538.2 ft²
16 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
US $138/Night
For 7 Nights US $963
8 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $288/Night
For 7 Nights US $2,017
Why Choose Rent By Owner for your Headley Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Headley
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as the best season for exploring this destination varies depending on whether you prefer mild weather or vibrant local events in the region.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather, attracting visitors seeking outdoor activities and scenic views. Booking a vacation rental here now ensures you enjoy the region’s lively summer atmosphere.
Average Temperature Daytime: around 20-25°C - Nighttime: around 13-17°C
Spring (March to May)
Spring is a popular time to visit when the natural beauty of the area comes alive with blooming flowers and lush landscapes. Securing your preferred property early provides a comfortable base to explore during this vibrant season.
Average Temperature Daytime: around 12-18°C - Nighttime: around 6-10°C
Off-Season Highlights
Autumn (September to November)
As the leaves change color, this destination offers a quieter, more relaxed experience. Booking outside peak months allows you to enjoy peaceful surroundings with fewer crowds.
Average Temperature Daytime: around 11-16°C - Nighttime: around 7-9°C
Winter (December to February)
During the colder months, the region takes on a tranquil appeal, making it ideal for those seeking solitude or cozy stays. Planning your retreat now guarantees availability in the off-peak season.
Average Temperature Daytime: around 4-8°C - Nighttime: around 2-4°C
Weekly Weather Forecast for Headley
How to Book Your Headley Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Headley
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas where you can relax and take in the scenic views of the countryside.
- Take advantage of private gardens or yards available for outdoor dining and leisure activities.
- Make the most of on-site barbecue facilities to host outdoor cookouts with family and friends.
- Explore nearby walking trails or cycling paths for outdoor adventure and exercise.
- Benefit from accessible parking amenities that make it easy to come and go during your stay here.
- Utilize outdoor storage spaces for equipment such as bicycles or sports gear.
- Relax by an outdoor fireplace or fire pit, perfect for cozy evenings under the stars in this destination's rural setting.
Top Attractions Around Headley
What attractions are nearby?
In this charming area, you can explore scenic walking trails and enjoy local outdoor activities that highlight the natural beauty of the region, making it an ideal destination for outdoor enthusiasts seeking a relaxing getaway.
Family Activities
- Headley Heath Nature Reserve: Explore this scenic nature reserve for enjoyable family walks and wildlife spotting amidst the region’s lush landscapes.
- Box Hill: Discover outdoor adventures on Box Hill, where you can hike, have picnics, and immerse yourselves in stunning views of the surrounding countryside.
- Petworth Park: Visit this historic park to enjoy leisurely strolls, observe local wildlife, and explore the beautiful gardens perfect for family outings.
- The National Trust's Dorking Museum: Delve into the area's history through engaging exhibits that are both educational and entertaining for children and adults alike.
Adult Activities
- Historic Walks and Heritage Trails: Discover the area's rich history by exploring scenic trails that showcase notable landmarks and local heritage, perfect for an enriching outdoor experience.
- Local Pubs and Gastronomy Tours: Immerse yourself in regional flavors by visiting popular pubs and dining establishments to enjoy traditional cuisine and authentic regional brews.
- Nature and Wildlife Observation: Spend time in serene natural settings where you can observe diverse wildlife and enjoy peaceful landscapes characteristic of this region.
- Golfing at Nearby Courses: Tee off at well-maintained golf courses nearby, offering a relaxing activity amid picturesque surroundings for leisure-minded travelers.
Headley Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit Carefully: Schedule your trip during the region's favorable seasons to enjoy outdoor activities and scenic beauty at their best.
- Explore Local Dining Options: Take advantage of nearby eateries that showcase traditional flavors, enriching your stay in this charming part of the United Kingdom.
- Utilize Nearby Transportation: Use local transportation links to easily access popular attractions and maximize your time exploring the area.
- Choose Comfortable Vacation Rentals: Select a well-rated property here that offers amenities suited to your needs, ensuring a relaxing and enjoyable experience during your stay.
Transportation Options
- Headley Train Station: This station offers easy access to the regional rail network, making it convenient for you to explore nearby towns and cities during your stay.
- Bus Services: Local bus routes connect the area with surrounding communities, providing flexible options for daily travel around this part of the United Kingdom.
- Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing options are available here, allowing you to reach your destination comfortably without the need for a personal vehicle.
- Car Rentals: Several car rental agencies operate in the region, giving you the freedom to discover more remote or scenic spots at your own pace.
Local Customs Options
- The Local Pub Culture: You can enjoy the region’s traditional pub gatherings, where locals share stories and local brews in a warm, welcoming atmosphere.
- Celebration of Traditional Events: Participating in annual events like local fairs and festivals provides a glimpse into the area's rich cultural heritage.
- Country Fair Customs: Engaging in country fairs involves observing age-old practices such as livestock shows and homemade craft displays that highlight regional traditions.
- Historic Church Services: Attending services at historic churches offers insight into the spiritual customs and architectural history cherished here.
Headley Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Headley?
There are a lot of options in Headley. If you plan on staying in the Headley area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Headley:
- Beautiful Victorian cottage in Ashtead easy access to London set in countryside
- Modern Serenity in Langley Vale
- Cozy Maisonette in Langley Vale
- Newly renovated flat in Ahsteadnn
- Westleigh
- Comfy Apartment 16 Easy access to Central London
- Highway Cottage - Mickleham
- Roomspace Serviced Apartments - Swan House
- Cozy Maisonette in Langley Vale
- The Lodge at Kingswood
2. Which vacation homes in Headley are best for families?
If you are looking for a family-friendly vacation home in Headley, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Headley:
3. How many Rentbyowner vacation rentals are available in Headley?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 93 in the Headley area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Headley.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the property owner and listing details. You should review the specific cancellation terms outlined on the listing page or contact the host directly to understand any applicable fees or restrictions.
5. How do I find out if a vacation rental is available during my travel dates?
Availability is shown directly on each property's listing. To confirm your dates, you can check the calendar provided or reach out to the owner for real-time availability updates.
6. Are there any specific check-in and check-out procedures for these vacation rentals?
Check-in and check-out times are generally specified in the listing details. For detailed instructions or special arrangements, it's best to contact the property owner ahead of your arrival.
7. What amenities are typically included in vacation rentals in this region?
Amenities vary by property, but common features include Wi-Fi, self-check-in options, and fully equipped kitchens. Review each listing for a comprehensive list of amenities offered.
8. How can I ensure that I'm booking a reputable vacation rental here?
Look for listings with verified reviews, detailed descriptions, and transparent contact information. You can also communicate directly with the owner to clarify any questions and build confidence in your booking.
Headley Top Rated Vacation Rentals
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $78/Night
For 7 Nights US $543
199.13 ft²
4 Guests
47 Bedrooms
2 Bathrooms
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- View
US $211/Night
For 7 Nights US $1,479
252.96 ft²
8 Guests
57 Bedrooms
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $160/Night
For 7 Nights US $1,122
