Discover Your Perfect Chestnut Hill Vacation Homes

Chestnut Hill Luxury Rentals

See More Chestnut Hill Luxury Vacation Rentals
Find More Chestnut Hill Villas, Resorts, & Rentals on BedroomVillas

Chestnut Hill Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Chestnut Hill on PetFriendly.io

Chestnut Hill Large Vacation Homes

See More Family Vacation Rentals in Chestnut Hill on FVR

Why Choose Rent By Owner for your Chestnut Hill Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Best Times to Visit Chestnut Hill

When should you plan your Vacation Rentals stay?

Finding the perfect time to visit this charming destination ensures you experience its beauty at its best, whether you're seeking peaceful getaways or vibrant seasons in the region.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the region experiences warm weather ideal for exploring outdoors and enjoying local events, making it a popular time for visitors seeking vibrant activity and pleasant temperatures.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to October)

This season attracts travelers who appreciate the stunning fall foliage and cooler temperatures, creating an inviting atmosphere for outdoor pursuits and scenic drives around here.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 45°F to 55°F

Off-Season Highlights

image
Winter (December to February)

The winter months see fewer visitors as the weather turns colder, offering a tranquil environment perfect for relaxing indoors or enjoying the peaceful natural surroundings at your leisure.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
image
Early Spring (March to April)

Before the area fully awakens with greenery, early spring provides a quieter experience with mild temperatures, ideal for those preferring a more secluded visit while waiting for the peak seasons to arrive.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Chestnut Hill

How to Book Your Chestnut Hill 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 Chestnut Hill

More Top-Rated Vacation Rentals in Chestnut Hill Area

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 access to private outdoor spaces such as yards or patios ideal for relaxation and outdoor dining.
  • Look forward to scenic views with options for outdoor seating areas to take in the natural beauty of the area.
  • Benefit from outdoor grilling facilities perfect for preparing meals during your stay.
  • Take advantage of nearby walking trails or nature paths that allow you to explore the region’s lush landscapes.
  • Relax by a private or community swimming pool, ideal for cooling off during warm summer days.
  • Utilize outdoor recreational amenities like fire pits or lounge areas suitable for gathering with friends and family.
  • Discover available boat docks or access points if you plan to enjoy water activities on the nearby lakes or rivers.

Top Attractions Around Chestnut Hill

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities and scenic spots nearby to explore in this charming region, making it easy to enjoy the natural beauty and relaxing atmosphere just minutes from your vacation rental.

image
image

Family Activities

  • Dandridge Historic District Tour: Explore the charming streets of the area's historic district to learn about local history and enjoy picturesque surroundings.
  • Tennessee Valley Trail Hikes: Discover scenic hiking trails nearby that are perfect for family adventures and offer stunning views of the region's natural beauty.
  • Lake Dandridge Boat Rentals: Spend a day on the water by renting boats or kayaks, providing fun and relaxation for the entire family in this peaceful lakeside setting.
  • Local Farmers Market Experience: Visit the area’s farmers market to enjoy fresh, regional produce and handmade crafts, making for a delightful family outing near your vacation rentals.
image

Adult Activities

  • Explore the Dandridge Historic District: Discover charming architecture and local history through guided tours and self-exploration in this area's well-preserved heritage sites.
  • Enjoy Lake Dandridge Activities: Engage in kayaking, paddleboarding, or relaxing lakeside picnics to make the most of the scenic waterfront here.
  • Visit the Smoky Mountain Heritage Center: Immerse yourself in regional culture and history with engaging exhibits that highlight the area’s rich Appalachian traditions.
  • Attend Local Festivals and Events: Experience the vibrant community spirit by participating in seasonal festivals, farmers markets, or live music gatherings held nearby.

Chestnut Hill Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area's delightful dining options to experience authentic flavors unique to this destination.
  • Plan Outdoor Activities: Make the most of the natural beauty by engaging in nearby outdoor pursuits such as hiking or relaxing by the waterfront.
  • Visit Seasonal Events: Check out local festivals or seasonal happenings to immerse yourself in the community’s vibrant culture during your stay.
  • Discover Nearby Attractions: Utilize this destination's prime location to visit scenic spots and hidden gems that complement your vacation experience.

Transportation Options

  • Interstate 40: This major highway provides convenient access to the area, making it easy to reach your vacation rental and explore nearby attractions in the region.
  • Dandridge Municipal Airport: A local airport offering limited regional flights, ideal for travelers arriving from other parts of Tennessee or neighboring states.
  • Local Taxi Services: Reliable taxi companies operate throughout the area, providing comfortable transportation options to get around here effortlessly.
  • Rental Car Services: Several rental agencies are available nearby, giving you the flexibility to explore this destination at your own pace without relying on public transit.

Local Customs Options

  • Southern Hospitality: The region is known for its warm and welcoming attitude, making guests feel right at home during their stay.
  • Enjoy the local appreciation for traditional folk music, often celebrated through community events and gatherings here.
  • Respect for Nature: Many residents uphold a strong custom of respecting the natural environment, reflecting the area's scenic mountain landscapes.
  • Community Festivals: Participating in or observing local festivals is a cherished tradition that highlights the area's cultural heritage and friendly spirit.

Frequently Asked Questions About Chestnut Hill?

1. What are the top vacation rentals in Chestnut Hill?

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

2. How many vacation rentals have private pools in Chestnut Hill?

There are 29 vacation rentals with private pools near Chestnut Hill. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chestnut Hill are best for families?

If you are looking for a family-friendly vacation home in Chestnut Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestnut Hill:

4. How many Rentbyowner vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 196 in the Chestnut Hill 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 Chestnut Hill. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies by property. You should review the specific terms listed in the rental details or contact the property owner directly to understand the cancellation timeframe and any applicable fees.

6. How do I secure my reservation for a vacation rental in Dandridge?

Reservations are typically confirmed through the booking platform or directly with the property owner. Ensure all required information is provided, and review the payment policies to finalize your booking securely.

7. Are there any specific check-in or check-out procedures I should be aware of?

Check-in and check-out times are specified in each property's listing. Some rentals may require additional steps like key exchanges or digital codes, so it’s best to confirm details with the host before your arrival.

8. What amenities can I expect at vacation rentals in the region?

Amenities vary across properties but commonly include Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. For a detailed list of what each rental offers, refer to the individual listing or contact the owner directly.

9. Is there a minimum stay requirement for booking here?

Minimum stay requirements differ depending on the property and season. Check the specific listing for this information, or reach out to the owner to clarify any duration restrictions.

Chestnut Hill Top Rated Vacation Rentals

See More Chestnut Hill Vacation Rentals