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Chestnut Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chestnut Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 1 - Jan 3

    Fox Run at Lake Lure + Flight

    Lake Lure
    2 nights
    4.5 star property
    9.0/10 - Wonderful (247 reviews)
    "Clean"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Asheville (AVL)
    YYZ - GSO • 1 stop GSO - YYZ • 1 stop
    CA $1,106
    CA $1,014
    per traveller
    found 2 hours ago
    Fox Run at Lake Lure
  • Jan 1 - Jan 3

    The Restoration Asheville + Flight

    Downtown Asheville
    2 nights
    4.0 star property
    9.8/10 - Exceptional (1,238 reviews)
    Roundtrip • Toronto (YTO) - Asheville (AVL)
    YYZ - GSO • 1 stop GSO - YYZ • 1 stop
    CA $1,669
    CA $1,315
    per traveller
    found 2 hours ago
    The Restoration Asheville
  • Feb 5 - Feb 7

    Smoketree Lodge + Flight

    Banner Elk
    2 nights
    3.0 star property
    8.6/10 - Excellent (324 reviews)
    "El area en general es muy bonita, es un hospedaje al lado de una via principal, asi que si buscas algo alejado del ruido de vehiculos depronto no es esta la mejor opcion. No habian mascotas ni fumadores, lo cual hizo mas agradable nuestra estancia. El lugar cuenta con una pequeña zona verde para disfrutar un buen cafe o para meditar si lo prefieres."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Asheville (AVL)
    YYZ - TRI • 1 stop TRI - YYZ • 1 stop
    CA $1,128
    CA $1,044
    per traveller
    found 13 hours ago
    Smoketree Lodge
  • Jan 1 - Jan 3

    Kimpton Hotel Arras by IHG + Flight

    Downtown Asheville
    2 nights
    4.0 star property
    9.6/10 - Exceptional (1,236 reviews)
    "Great location, friendly staff and easy onsite valet parking. Would definitely stay here again!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Asheville (AVL)
    YYZ - GSO • 1 stop GSO - YYZ • 1 stop
    CA $1,235
    CA $1,161
    per traveller
    found 2 hours ago
    Kimpton Hotel Arras by IHG
  • Jan 1 - Jan 3

    Rhode's Motor Lodge + Flight

    Boone
    2 nights
    2.0 star property
    9.4/10 - Exceptional (991 reviews)
    "Clean and nice spot"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Asheville (AVL)
    YYZ - GSO • 1 stop GSO - YYZ • 1 stop
    CA $1,126
    CA $1,079
    per traveller
    found 2 hours ago
    Rhode's Motor Lodge

Where to stay in Chestnut Hills

Find the best Chestnut Hills areas and neighborhoods for the activities you enjoy most.

Downtown Asheville

Travelers to Downtown Asheville praise its popular shops. If you've got some more time to explore, be sure to make a stop by Grove Arcade and Pack Square.

South Asheville

While visiting South Asheville, you might make a stop by sights like Biltmore Estate and Biltmore Park Town Square.

Biltmore Village

Adjacent to the Biltmore Estate entrance, this small village boasts the stunning Cathedral of All Souls and a lively commercial district with eclectic shops and restaurants.

West Asheville

The picture-perfect mountain views and abundant dining options are top of the list for many visitors to West Asheville. A stop by French Broad River or Asheville Outlets might round out your trip.

Downtown Asheville Art District

Travelers come to Downtown Asheville Art District for its abundant dining options, and you can see top attractions like Pack Square and Grove Arcade while you're in town.

Chestnut Hills Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Chestnut Hills vacation package cost?

The cheapest Chestnut Hills vacation package is CA $1,014, so your dream escape can become a reality — without a hefty price tag. Bundle flights, hotels and car rentals to tailor a package that suits your travel style.

How do I get a cheap travel package to Chestnut Hills?

Our Chestnut Hills vacation packages offer plenty of savings for the savvy traveler. For the best deal, simply bundle your hotel, flights and extras (including tours) into one neat package. But impressive bargains are only the start of your next memorable adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels across the globe to choose from. No matter your style, there's a package that's perfect for you.

Where should I stay in Chestnut Hills?

Most travelers who visit Chestnut Hills include both Biltmore Estate and Asheville Mall on their must-see lists. Why not reserve a hotel near these iconic attractions?

What are the top hotels in Chestnut Hills?

Chestnut Street Inn B&B and Cozy Apartment With Mountain Views are among the most well-known hotels in Chestnut Hills. Why not check out the amenities and facilities at each and then decide?

How far in advance should I book my Chestnut Hills vacation?

It depends on the airline, but it's usually possible to look up international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally nab a cheaper seat just weeks prior to the date of departure.

What does an Expedia Chestnut Hills travel package include?

Flights, hotels and rental cars — we have them well covered. With Expedia, you can shape your Chestnut Hills travel package however you want. All you have to do is decide exactly what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the greater your savings!

What should I know before booking a Chestnut Hills travel package?

Whether it's adventure or relaxation you're chasing, a Chestnut Hills vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the bigger the savings!

Can I choose my airline with a Chestnut Hills Expedia vacation package?

Yes, you sure can. We offer more than 550 partner airlines across the globe, so select the carrier that suits your travel needs.

If I'm not able to travel, can I cancel my Chestnut Hills vacation package?

You sure can, and we're here to help. You may be able to amend or cancel your Chestnut Hills vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, browse our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.