Discover Your Perfect Chestnut Hills Vacation Homes

Best Vacation Homes in Chestnut Hills

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10.0 (8 Reviews)
Apartment
The Views Over Pack Square
  • Accessibility
  • Security/Safety
  • Sports/Activities
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Chestnut Hills Luxury Rentals

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Chestnut Hills Pet Friendly Vacation Rentals

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10.0 (6 Reviews)
Apartment
Endless Sunset Retreat
  • Pet Friendly
  • Accessibility
  • Security/Safety
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Chestnut Hills Large Vacation Homes

10.0 (3 Reviews)
Apartment
Ravenscroft Rentals
  • Air Conditioner
  • Parking
  • Security/Safety
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Why Choose Rent By Owner for your Chestnut Hills 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.

Popular Areas for Chestnut Hills Vacation Rentals

Where are the best neighborhoods to stay in Chestnut Hills?

When exploring neighborhoods to stay in Chestnut Hills, Asheville, North Carolina, you'll find a charming community that offers a peaceful retreat while being close to the vibrant attractions of Asheville. This area provides an ideal setting for those seeking scenic beauty and local charm, making it a perfect choice for your next getaway. With a variety of cozy vacation rentals available, you can enjoy a comfortable and memorable stay in this picturesque part of Asheville. Whether you're drawn to its serene atmosphere or its convenient location, Chestnut Hills offers an authentic experience of North Carolina’s mountain hospitality.

Claxton Community

This neighborhood offers a tranquil setting within Asheville, providing convenient access to local amenities and scenic views that enhance your stay in the area.

View 1454+ Rentals in Claxton Community

Murdock - Linden

Ideally situated, this neighborhood allows you to enjoy the charm of Asheville while remaining close to parks and cultural sites, perfect for exploring during your visit.

View 1414+ Rentals in Murdock - Linden

Charlotte Street

Located near the heart of Asheville, Charlotte Street provides easy access to dining, arts, and entertainment options that make your stay lively and memorable.

View 1390+ Rentals in Charlotte Street

Albemarle Park

Known for its historic architecture and peaceful ambiance, Albemarle Park is an ideal spot for those seeking a charming neighborhood with picturesque surroundings.

View 1406+ Rentals in Albemarle Park

Best Times to Visit Chestnut Hills

When should you plan your Vacation Rentals stay?

To make the most of your stay in this charming area, consider visiting during the shoulder seasons when the region's natural beauty is at its peak and crowds are smaller, ensuring a more relaxing experience in your ideal vacation rental.

Peak Season Highlights

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Spring (March to May)

During spring, the area blossoms with vibrant foliage, making it an ideal time to enjoy the scenic beauty of this destination.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Autumn offers breathtaking fall foliage and cooler temperatures, perfect for exploring the region's natural attractions.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

Winter sees fewer visitors, but you can still enjoy the peaceful atmosphere and scenic winter landscapes here.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 25°F to 35°F
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Summer (June to August)

While summer brings warmer weather, it is also the quieter season with fewer crowds, providing a serene retreat in this region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Chestnut Hills

How to Book Your Chestnut Hills 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 Hills

More Top-Rated Vacation Rentals in Chestnut Hills 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 a private outdoor seating area or patio to relax and take in the scenic views of the region.
  • Take advantage of a backyard or garden space perfect for outdoor dining or picnics in the area’s natural surroundings.
  • Make use of outdoor fire pits or fireplaces to gather with friends or family during cooler evenings.
  • Benefit from access to hiking trails, walking paths, or nature walks directly from your rental stay.
  • Utilize a swimming pool, hot tub, or spa to unwind amidst the peaceful atmosphere of the region.
  • Explore lush landscapes with well-maintained lawns, gardens, or outdoor recreational areas on the property.
  • Leverage outdoor amenities like grills or barbecues, ideal for preparing meals while enjoying the fresh mountain air here in Asheville’s scenic area.

Top Attractions Around Chestnut Hills

What attractions are nearby?

While staying here, you'll find a variety of outdoor activities and scenic attractions nearby, perfect for exploring the natural beauty and vibrant culture of Asheville's Chestnut Hills area.

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Family Activities

  • Blue Ridge Parkway Scenic Drive: Enjoy a family-friendly drive along the Blue Ridge Parkway, offering breathtaking views and access to hiking trails perfect for exploring the region’s natural beauty.
  • Asheville Botanical Garden: Discover this lush garden with engaging programs for children, showcasing native plants and inspiring outdoor exploration in the area.
  • North Carolina Arboretum: Experience educational exhibits, beautiful gardens, and outdoor activities that are ideal for family outings in this scenic part of Asheville.
  • U.S. Cellular Center Asheville: Attend family-friendly events and entertainment options at this well-known venue, providing fun-filled experiences for visitors staying here.
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Adult Activities

  • Hiking and Nature Walks: Explore the scenic trails that wind through the lush landscapes surrounding this destination, offering a peaceful retreat into nature.
  • Cultural Arts Experiences: Visit local galleries and cultural centers to immerse yourself in the vibrant arts scene of the region.
  • Dining at Gourmet Restaurants: Savor gourmet cuisine at renowned restaurants that showcase the area's farm-to-table culinary delights.
  • Craft Breweries and Wineries: Enjoy tastings at the area’s craft breweries and scenic wineries, perfect for relaxing adult outings.

Chestnut Hills Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the scenic trails nearby to enjoy the natural beauty and tranquility that make this destination unique.
  • Discover Culinary Gems: Sample the region's local cuisine at nearby eateries to immerse yourself in the authentic flavors of here.
  • Plan Outdoor Activities: Engage in outdoor adventures such as hiking or exploring parks to fully experience the area's lush landscape.
  • Visit Nearby Art and Cultural Spots: Spend time exploring local galleries and cultural venues to get a deeper appreciation of the regional arts scene.

Transportation Options

  • Car Rental Services: Local car rental agencies provide convenient options for exploring the scenic areas and attractions around Asheville's Chestnut Hills.
  • Public Transit: Bus services connect this part of Asheville with downtown and surrounding neighborhoods, offering an affordable transportation method within the region.
  • Ridesharing: Companies like Uber and Lyft operate in the area, giving you flexible and on-demand travel options during your stay here.
  • Bicycle Rentals: Rent bikes nearby to enjoy the picturesque roads and trails that highlight the natural beauty of the Asheville region.

Local Customs Options

  • Southern Hospitality: Locals here are known for their warm and welcoming demeanor, making your stay in this area feel like visiting family.
  • Festival Traditions: Participating in seasonal festivals is a cherished custom, offering a unique glimpse into the community’s vibrant culture.
  • Artisan Craftsmanship: Supporting local artisans through handmade crafts and galleries is an integral part of experiencing the region's artistic spirit.
  • Farm-to-Table Cuisine: Dining at establishments that emphasize fresh, locally sourced ingredients reflects the area's deep-rooted food traditions.

Frequently Asked Questions About Chestnut Hills?

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

There are a lot of options in Chestnut Hills. If you plan on staying in the Chestnut Hills 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 Hills:

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

There are 26 vacation rentals with private pools near Chestnut Hills. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Chestnut Hills, 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 Hills:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1287 in the Chestnut Hills 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 Hills. 

5. What is the cancellation policy for booking a vacation rental in Chestnut Hills?

Cancellation policies vary depending on the individual property listing. You should review the specific cancellation terms outlined in the rental description or contact the property owner directly to understand the policy before completing your reservation.

6. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning, service charges, or security deposits are detailed in each listing. It is recommended to read the full fee breakdown provided and reach out to the owner if you have any questions about extra costs involved.

7. How do I know if my preferred dates are available for a vacation rental here?

Availability calendars are typically updated regularly on the listing page. To ensure your dates are open, confirm availability directly through the booking system or contact the property owner for real-time updates.

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

Amenities vary by property but often include essentials like Wi-Fi, parking, and fully equipped kitchens. For specific features, review the property details or ask the owner directly to match your needs during your stay.

9. How do I secure my reservation at a vacation rental in this destination?

Reservations are generally secured through a secure booking process provided by the listing platform. You may need to pay a deposit or full amount upfront, and it's advisable to communicate with the owner for any special requests or questions regarding your booking.

Chestnut Hills Top Rated Vacation Rentals

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