Cheshire Vacations from $273

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Your Cheshire Vacation

Your next big journey is calling your name with a vacation package to Cheshire. Entertainment, relaxation and nonstop great times — you're bound to find it in this neighborhood. When it's time to head out and explore, you'll find plenty of top attractions nearby including Lake Tomahawk, Black Mountain Center for the Arts and White Horse Black Mountain. Visit one, two (or even all!) during your trip to Cheshire. Expedia is here to put your plans into action. Book your perfect Cheshire vacation today.

The Latest Cheshire Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairway Forest

Fairway Forest

3.5 out of 5
Save 100% on your flight
Price was $429, price is now $273 per person
$273
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Asheville (AVL)
8.8/10 Excellent! (287 reviews)
Pool was great for kids

Reviewed on Oct 14, 2025

Element Asheville Downtown

Element Asheville Downtown

3 out of 5
Downtown Asheville
Price was $611, price is now $409 per person
$409
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Asheville (AVL)
9.4/10 Exceptional! (432 reviews)
Clean room. Friendly staff. Delicious healthy breakfast.

Reviewed on Oct 17, 2025

Foxhunt at Sapphire Valley

Foxhunt at Sapphire Valley

3.5 out of 5
Price was $1,326, price is now $900 per person
$900
per person
Nov 30 - Dec 4
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Asheville (AVL)
9/10 Wonderful! (428 reviews)
Very clean and friendly

Reviewed on Oct 27, 2025

The Omni Grove Park Inn & Spa

The Omni Grove Park Inn & Spa

4 out of 5
Grove Park- Sunset
Price was $1,874, price is now $1,290 per person
$1,290
per person
Nov 30 - Dec 4
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Asheville (AVL)
9.2/10 Wonderful! (1,013 reviews)
Just absolutely amazing. I am in the travel industry and was over joyed about just about everything at this property. We traveled there in early October, it was busy but didn’t feel over-run. The staff is amazingly friendly and helpful. No reason, at all, to leave property for meals - we did visit 2 restaurants that the Omni concierge even recommended and were not as happy with the food/service as we were at the hotel. Overall one of our best vacations - will for sure be back!

Reviewed on Oct 27, 2025

The Windsor Boutique Hotel

The Windsor Boutique Hotel

4 out of 5
Downtown Asheville
Save 100% on your flight
Price was $1,331, price is now $923 per person
$923
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Asheville (AVL)
9.8/10 Exceptional! (534 reviews)
Great staff - very comfortable accommodations, great location

Reviewed on Oct 25, 2025

Cheshire Hotel Deals

Country Inn & Suites by Radisson Asheville Downtown Tunnel Road

Country Inn & Suites by Radisson Asheville Downtown Tunnel Road

3 out of 5
199 Tunnel Rd, Asheville, NC
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $91 total per night from Nov 23 to Nov 24
$91 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,793 reviews)
First, let's be clear...this hotel is not in downtown Asheville. It is located over a mile east of downtown. Those wishing to stay downtown Asheville should look for a different choice. The hotel itself was clean and well decorated. The beds in the room that my wife and I stayed in were very comfortable. ...

Reviewed on Oct 27, 2025

Country Inn & Suites by Radisson Asheville Downtown Tunnel Road
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
$383 nightly
The price is $433 total per night from Nov 17 to Nov 18
$433 total
Nov 17 - Nov 18
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Most hospitable staff, absolutely beautiful lobby and many delicious restaurants.

Reviewed on Oct 25, 2025

The Omni Grove Park Inn & Spa
Holiday Inn Express & Suites Asheville Downtown by IHG

Holiday Inn Express & Suites Asheville Downtown by IHG

2.5 out of 5
42 Tunnel Rd, Asheville, NC
Fully refundable
$102 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
Great place to staff , front desk folks very nice

Reviewed on Oct 23, 2025

Holiday Inn Express & Suites Asheville Downtown by IHG
See all 3,899 properties in Cheshire
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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Discover the most popular places to visit in Cheshire

#aboveitall #lifeatexpedia Catawba Falls near Asheville, NC!

Catawba Falls

4.5/5(5 reviews)

Enjoy the mountain views and explore Catawba Falls, a lovely green space in Black Mountain. Stroll along the area's lakeside or simply enjoy its breweries.

Catawba Falls

Black Mountain Center for the Arts

You can spend time browsing the exhibits at Black Mountain Center for the Arts in Black Mountain. Discover the mountain views and top-notch restaurants in this family-friendly area.

Black Mountain Center for the Arts

Swannanoa Valley Museum

You can spend time studying the exhibits at Swannanoa Valley Museum in Black Mountain. Discover the area's mountain views and top-notch restaurants.

Swannanoa Valley Museum

Things to do

Blue Ridge Parkway Asheville Self-Guided Audio Tour

Blue Ridge Parkway Asheville Self-Guided Audio Tour

$13
per traveler
Blue Ridge Parkway Asheville Self-Guided Audio Tour
See all activities in Black Mountain
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.