Discover Your Perfect Chartwell Vacation Homes

Best Vacation Homes in Chartwell

House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
3 Bedrooms 2 Baths 5 Guests 11 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
CA $704/Night 7 Nights - CA $4,925
star-icons-4
House
Map-icon
like-icon9.8
Exceptional
(11 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
CA $349/Night 7 Nights - CA $2,445
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.8
Exceptional
(23 Reviews)
1 Bedroom 1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
CA $241/Night 7 Nights - CA $1,685
Cottage
Map-icon
like-icon9.6
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $429/Night 7 Nights - CA $3,005
star-icons-4
House
Map-icon
like-icon9.6
Exceptional
(11 Reviews)
2 Bedrooms 1 Bath 4 Guests 904.17 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $342/Night 7 Nights - CA $2,395
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.6
Exceptional
(58 Reviews)
1 Bedroom 1 Bath
  • Pool
    Pool
  • Parking
    Parking
More amenities
CA $359/Night 7 Nights - CA $2,516
House
Map-icon
1 Bedroom 1 Bath 4 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
CA $1,887/Night 7 Nights - CA $13,209
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.2
Exceptional
(121 Reviews)
4 Bedrooms 4 Baths 10 Guests 150.7 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $671/Night 7 Nights - CA $4,695
star-icons-4
Hotel
Map-icon
like-icon9.6
Exceptional
(211 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Breakfast
    Breakfast
More amenities
CA $221/Night 7 Nights - CA $1,545
House
Map-icon
2 Bedrooms 1 Bath 6 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
CA $1,850/Night 7 Nights - CA $12,949
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.2
Exceptional
(56 Reviews)
2 Bedrooms 2 Baths 4 Guests 242.19 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
CA $239/Night 7 Nights - CA $1,674
star-icons-3
Hotel
Map-icon
like-icon8.0
Excellent
(966 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $66/Night 7 Nights - CA $459

Why Choose Rent By Owner for your Chartwell Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chartwell

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the region’s unique charm at its best, whether you prefer the vibrant atmosphere of warmer months or the tranquil beauty of the quieter seasons.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area enjoys mild weather and blooming landscapes, making it an ideal time for exploring the region’s scenic beauty from your vacation rental.

Average Temperature Daytime: 15-20°C - Nighttime: 10-15°C
summer
Summer Months (July to August)

The peak of summer offers longer daylight hours and warm temperatures, perfect for outdoor activities and enjoying the local countryside from your accommodation here.

Average Temperature Daytime: 20-25°C - Nighttime: 13-17°C

Off-Season Highlights

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Early Autumn (September to October)

As the weather begins to cool, fewer visitors explore the region, allowing you to enjoy a more tranquil experience at your vacation rental while witnessing the early changes in foliage.

Average Temperature Daytime: 12-18°C - Nighttime: 8-12°C
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Winter Months (December to February)

The colder months bring a quieter atmosphere, making it a peaceful time to stay in your rental as the region takes on a serene winter charm with minimal crowds.

Average Temperature Daytime: 6-9°C - Nighttime: 2-4°C

Weekly Weather Forecast for Chartwell

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.

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 dining areas perfect for al fresco meals amidst the scenic beauty of the region.
  • Take advantage of well-maintained gardens or landscaped yards that provide a peaceful outdoor retreat.
  • Relish in private patios or terraces ideal for relaxing with a morning coffee or evening drinks.
  • Make use of spacious lawns or grassy areas suitable for outdoor games and activities.
  • Explore nearby walking or hiking trails that showcase the natural charm of this destination.
  • Benefit from on-site parking facilities to conveniently explore the wider area at your leisure.
  • Experience outdoor amenities designed to enhance your stay, such as fire pits or BBQ grills, within this idyllic setting.
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Family Activities

  • Chartwell House and Gardens Tour: Explore the historic home of Sir Winston Churchill, offering engaging exhibits and beautiful gardens that families can enjoy together in this charming area.
  • Westerham Golf Club: Spend quality time at a family-friendly golf club nearby, where beginners and experienced players alike can enjoy a round amidst scenic surroundings.
  • Westerham Nature Walks: Embark on picturesque walking trails through the lush countryside, perfect for outdoor adventures and discovering the area's natural beauty with your loved ones.
  • Local Farmers’ Markets: Experience the vibrant local markets in the region, ideal for sampling fresh produce and authentic regional flavors during your family getaway.
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Adult Activities

  • Wander through the National Trust property of Chartwell House: Discover the historic home and beautiful gardens that offer a peaceful retreat and insight into Sir Winston Churchill's life, perfect for a leisurely exploration during your stay.
  • Enjoy scenic walks in the surrounding countryside: The region offers numerous trails and nature paths where you can immerse yourself in the tranquil landscape and observe local flora and fauna.
  • Experience local dining at charming pubs and cafes: Savor traditional British cuisine and regional specialties at welcoming establishments close to your accommodation in this area.
  • Visit nearby historic towns and villages: Explore quaint streets and historical sites in Westerham and beyond, enriching your stay with cultural discoveries and authentic local charm.

Chartwell Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Heritage: Take time to visit the nearby historic sites and gardens to truly appreciate the rich cultural background of this area.
  • Experience Outdoor Activities: Make the most of the region’s scenic landscapes by enjoying walking trails or outdoor pursuits right from your vacation rental.
  • Discover Culinary Gems: Sample local cuisine at nearby cafes and restaurants to get a taste of the area's culinary traditions.
  • Plan Ahead for Attractions: Book tickets in advance for popular local attractions to avoid long waits and ensure a smooth, enjoyable stay here.

Transportation Options

  • Westerham Railway Station: Located just a short drive away, this station offers convenient train services connecting you to London and other major UK cities.
  • Local Bus Services: Regular bus routes operate throughout the area, providing easy access to nearby towns and attractions without the need for a car.
  • Car Rental Facilities: Several local providers offer rental cars here, giving you the flexibility to explore the region at your own pace.
  • Taxis and Ride-Sharing: Taxis and ride-sharing options are readily available for comfortable and direct transportation within and around this destination.

Local Customs Options

  • Traditional Afternoon Tea: Indulging in a classic afternoon tea here offers a glimpse into the region’s rich hospitality customs, which you can enjoy during your stay at this destination.
  • Local Village Fairs: Participating in seasonal village fairs is a cherished tradition, showcasing local crafts and foods that reflect the area's vibrant community spirit.
  • Respect for Historic Sites: Visitors often observe a respectful attitude toward historic landmarks and countryside, emphasizing the region’s appreciation for its cultural heritage.
  • Garden Celebrations: Engaging in garden visits and outdoor celebrations highlights the area's love for green spaces and outdoor social customs.

Frequently Asked Questions About Chartwell?

1. What are the top vacation rentals in Chartwell?

There are a lot of options in Chartwell. If you plan on staying in the Chartwell area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chartwell:

2. How many Rentbyowner vacation rentals are available in Chartwell?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 25 in the Chartwell 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 Chartwell. 

3. What is the cancellation policy for booking a vacation rental in this area?

Cancellation policies vary depending on the individual owner or property listing. You should review the specific cancellation terms outlined in the listing details or contact the owner directly for clarification.

4. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, security deposits, or service charges may apply and will be specified within the listing. It’s best to check the details provided or reach out to the property owner for complete fee information.

5. How do I ensure the availability of a vacation rental in this destination during my preferred dates?

Availability depends on current bookings, which can be confirmed by checking the calendar on the listing page. For certainty, contacting the owner directly can help verify your desired travel dates.

6. What amenities are typically included in vacation rentals in this region?

Most listings feature essential amenities like Wi-Fi, parking, and fully equipped kitchens. Specific amenities vary between properties, so reviewing each listing carefully or contacting the owner offers the most accurate information.

7. Do I need to have any special requirements or provide documentation to book a rental here?

Booking requirements differ by owner; some may request identification or other documentation. It’s advisable to read the booking instructions thoroughly or communicate directly with the owner to understand their specific process.

Best Vacation Homes in Chartwell

Cottage
Map-icon
3 Bedrooms 2 Baths 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $627/Night 7 Nights - CA $4,388
House
Map-icon
like-icon8.7
Fabulous
(3 Reviews)
4 Bedrooms 2 Baths 8 Guests 2701.74 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
More amenities
CA $652/Night 7 Nights - CA $4,562
star-icons-3
Hotel
Map-icon
like-icon7.4
Very Good
(312 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $153/Night 7 Nights - CA $1,070
House
Map-icon
4 Bedrooms 3 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $456/Night 7 Nights - CA $3,195
star-icons-5
House
Map-icon
like-icon7.9
Very Good
(39 Reviews)
2 Bedrooms 1 Bath 3 Guests 118.4 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Internet
    Internet
More amenities
CA $236/Night 7 Nights - CA $1,648
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 3 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
CA $257/Night 7 Nights - CA $1,799
star-icons-4
House
Map-icon
1 Bedroom 2 Baths 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
CA $576/Night 7 Nights - CA $4,030
Cottage
Map-icon
like-icon9.8
Exceptional
(95 Reviews)
3 Bedrooms 2 Baths 5 Guests 1442 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $428/Night 7 Nights - CA $2,995
New
House
Map-icon
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
CA $354/Night 7 Nights - CA $2,475
Cottage
Map-icon
3 Bedrooms 3 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
CA $341/Night 7 Nights - CA $2,390
Hotel
Map-icon
like-icon9.0
Exceptional
(730 Reviews)
5 Baths 60.28 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $252/Night 7 Nights - CA $1,763
star-icons-3
Hotel
Map-icon
like-icon7.5
Very Good
(2034 Reviews)
7 Baths 235.27 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $105/Night 7 Nights - CA $738