Chestnut Hills Vacations from $417

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Your Chestnut Hills Vacation

Step into your next big travel adventure with one of our Chestnut Hills vacation packages. Spend your time uncovering this neighborhood's many charms, such as its history. Some top nearby attractions to see during your trip to Chestnut Hills include Asheville Mall, Harrahs Cherokee Center - Asheville and The Orange Peel. Expedia will help put your plans into action. Book your ideal Chestnut Hills vacation today.

The Latest Chestnut Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Asheville Downtown

Hilton Garden Inn Asheville Downtown

3 out of 5
Downtown Asheville
Price was $668, price is now $417 per person
$417
per person
Feb 21 - Feb 25
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.2/10 Wonderful! (895 reviews)
The room was very clean and staff were wonderful. The Christmas decorations were beautiful and especially fun at the Rooftop Bar. Drinks and Food were delicious!

Reviewed on Dec 1, 2025

Cedar Crest Inn

Cedar Crest Inn

3.5 out of 5
Kenilworth
Save 100% on your flight
Price was $972, price is now $543 per person
$543
per person
Feb 21 - Feb 25
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.4/10 Exceptional! (373 reviews)
Room was very clean and cozy. The staff was very cordial and pleasant. The house was beautiful with lots of dark wood interior.

Reviewed on Dec 11, 2025

Element Asheville Downtown

Element Asheville Downtown

3 out of 5
Downtown Asheville
Save 100% on your flight
Price was $904, price is now $562 per person
$562
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.4/10 Exceptional! (438 reviews)
Most Staff was very friendly! Breakfast was good except when they ran out early and the coffee machine was broken. Relax hour was good except when the wine keg was broken.

Reviewed on Nov 28, 2025

The Horse Shoe Farm

The Horse Shoe Farm

3.5 out of 5
Save 100% on your flight
Price was $1,111, price is now $698 per person
$698
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Asheville (AVL)
9.6/10 Exceptional! (7 reviews)
Every staff member went out of his/her way to make us more comfortable.

Reviewed on Jul 27, 2024

The Windsor Boutique Hotel

The Windsor Boutique Hotel

4 out of 5
Downtown Asheville
Save 100% on your flight
Price was $1,362, price is now $883 per person
$883
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.8/10 Exceptional! (543 reviews)
One of my all time favorite boutique hotels I have ever stayed! Room was incredible, friendly staff who were so nice, and just an all around exceptional experience! We will be back, I just wish we could have stayed here for an entire month!!

Reviewed on Dec 7, 2025

Where to stay in Chestnut Hills

Find the best Chestnut Hills areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hills
Asheville

Downtown Asheville

2 out of top 10 points of interest in this area
4.5/5(969 area reviews)

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.

Find hotels in Downtown Asheville

Chestnut Hills Hotel Deals

Beaufort House Inn

Beaufort House Inn

4 out of 5
61 N Liberty St Asheville NC
Fully refundable
$172 nightly
The price is $194 total per night from Jan 8 to Jan 9
$194 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
9.4/10 Exceptional! (324 reviews)
The staff were excellent and the room was large and comfortable. Breakfast was carb heavy (bagels and muesli only), so we ended up going out for breakfast most days. Highly recommend walking down to Five Points diner for an excellent breakfast. We probably will not stay here again but the stay was ...

Reviewed on Nov 15, 2025

Beaufort House Inn
The Omni Grove Park Inn & Spa

The Omni Grove Park Inn & Spa

4 out of 5
290 Macon Avenue Asheville NC
Fully refundableReserve now, pay when you stay
$337 nightly
The price is $380 total per night from Jan 6 to Jan 7
$380 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
Great location - great service from all staff - great prepared meals - mild not have been better!

Reviewed on Dec 8, 2025

The Omni Grove Park Inn & Spa
The Restoration Asheville

The Restoration Asheville

4 out of 5
68 Patton Ave Asheville NC
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $261 total per night from Dec 16 to Dec 17
$261 total
Dec 16 - Dec 17
Total with taxes and fees
9.8/10 Exceptional! (1,020 reviews)
The hotel is very nice, central located and the staff very friendly. My only disappointment was with the breakfast that is left in a basket outside the room

Reviewed on Dec 9, 2025

The Restoration Asheville
See all 3,591 properties in Chestnut Hills
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.
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All Inclusive Vacations
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Discover the most popular places to visit in Chestnut Hills

Biltmore Estate featuring a park, a statue or sculpture and interior views

Biltmore Estate

5/5(1,849 reviews)

Wander through gardens and lush grounds, tour the grand mansion and learn about the history of this opulent estate in Asheville, North Carolina.

Biltmore Estate
Mini fair and Biltmore square mall

Asheville Outlets

4.5/5(595 reviews)

You can search for that perfect souvenir at Asheville Outlets during your trip to Asheville. Discover the area's top-notch restaurants and its acclaimed theater scene.

Asheville Outlets
The Orange Peel

The Orange Peel

4.5/5(158 reviews)

The Orange Peel is just one of the places to see in Asheville, so why not enjoy the other things to explore during your travels? Experience the area's acclaimed theater scene and lively festivals.

The Orange Peel

Things to do

Picture 14 for Activity Asheville Terrors: Blue Ridge Haunted Walking Tour

The Asheville Apparitions of the Abyss Ghost Tour

$36
per adult
The Asheville Apparitions of the Abyss Ghost Tour
Custom Half-Day Photo Tour with Photography Lessons from Asheville

Custom Half-Day Photo Tour with Photography Lessons from Asheville

$170
per adult
Custom Half-Day Photo Tour with Photography Lessons from Asheville
Asheville Insider Guided Walking Tour

Asheville Insider Guided Walking Tour

$35
per adult
96% of travellers recommend
Asheville Insider Guided Walking Tour
See all activities in Asheville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.