Cheshire Vacation Packages

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Top Holiday Package Deals in Cheshire

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Asheville East-Blue Ridge PKWY by IHG

Holiday Inn Asheville East-Blue Ridge PKWY by IHG

3 out of 5
Price was CA $1,208, price is now CA $878 per person
CA $878
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Asheville (AVL)
9.4/10 Exceptional! (1,005 reviews)
Around the pool should’ve been clean better. The restaurant wasn’t open the whole time we were there for dinner.

Reviewed on Aug. 28, 2025

Hilton Garden Inn Asheville Downtown

Hilton Garden Inn Asheville Downtown

3 out of 5
Downtown Asheville
Price was CA $1,644, price is now CA $1,108 per person
CA $1,108
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Asheville (AVL)
9.2/10 Wonderful! (858 reviews)
Overall a great experience. Top of my list for Asheville hotels downtown.

Reviewed on Aug. 27, 2025

The Windsor Boutique Hotel

The Windsor Boutique Hotel

4 out of 5
Downtown Asheville
Price was CA $2,625, price is now CA $1,946 per person
CA $1,946
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Asheville (AVL)
9.8/10 Exceptional! (527 reviews)
I recently stayed at the Windsor Boutique Hotel, and it was fantastic! The staff were incredibly welcoming, and the chic decor perfectly blends modern elegance with local charm. My room was very cozy and was impeccably clean. The location is ideal, just a short walk from downtown Asheville's shops and restaurants. Breakfast featured delicious, locally sourced ingredients. The personalized service and attention to detail made my stay unforgettable. Highly recommend the Windsor Boutique Hotel for a memorable Asheville experience!

Reviewed on Aug. 17, 2025

Kimpton Hotel Arras by IHG

Kimpton Hotel Arras by IHG

4 out of 5
Downtown Asheville
Price was CA $2,304, price is now CA $1,713 per person
CA $1,713
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Asheville (AVL)
9.8/10 Exceptional! (1,016 reviews)
Great hotel in great location. Front of house staff was exceptional. Bar staff unfortunately was quite rude and unfriendly. Maybe they were just understaffed, but don’t take that out on the customer.

Reviewed on Aug. 24, 2025

The Restoration Asheville

The Restoration Asheville

4 out of 5
Downtown Asheville
Price was CA $2,980, price is now CA $2,229 per person
CA $2,229
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Asheville (AVL)
9.8/10 Exceptional! (909 reviews)
Room was very nice. Centrally located to the heart of the city. Helpful staff, great visit. We repeat this location when coming to Asheville!

Reviewed on Aug. 27, 2025

Cheshire Hotel Deals

Crowne Plaza Resort Asheville by IHG

Crowne Plaza Resort Asheville by IHG

3.5 out of 5
1 Resort Dr, Asheville, NC
Fully refundable
The price is CA $109 per night from Sep 3 to Sep 4
CA $109
CA $123 total
Sep 3 - Sep 4
includes taxes & fees
Crowne Plaza Resort Asheville by IHG
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
The price is CA $397 per night from Sep 1 to Sep 2
CA $397
CA $511 total
Sep 1 - Sep 2
includes taxes & fees
The Omni Grove Park Inn & Spa
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 refundable
The price is CA $112 per night from Sep 28 to Sep 29
CA $112
CA $127 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (1,640 reviews)
"Wonderful Stay!"

Reviewed on Aug. 27, 2025

Country Inn & Suites by Radisson Asheville Downtown Tunnel Road
See all 3,927 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
We make it easy to travel somewhere new, with Cheshire vacation packages starting from as low as CA $878. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of activities and tours to your itinerary?
How do I get a cheap travel package to Cheshire?
You'll save a ton of money if you combine your car rentals, flights and hotels into a Cheshire travel package. Sometimes cheap means fewer options. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels across the globe, so you'll always have plenty of variety to choose from. Like to save even more? Add some popular activities to your package deal and unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Cheshire?
A trip to Cheshire wouldn't be complete without visiting Black Mountain Center for the Arts, Lake Tomahawk and Black Mountain Golf Club. Spend your nights near these popular attractions and make sightseeing easy.
What are the top hotels in Cheshire?
Secure a room at Stepping Stone, Black Mountain Home. It's one of this neighborhood's most popular properties. Another well-known option in Cheshire is Charming Black Mountain Retreat.
How far in advance should I book my Cheshire vacation?
It all depends on the air carrier, but you can normally browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia Cheshire travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply choose your favorite bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings pile up. When it comes to organizing your Cheshire break, you're in control!
What should I know before booking a Cheshire travel package?
Whether it's relaxation or adventure you're chasing, a Cheshire vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Cheshire Expedia vacation package?
You sure can. We have more than 550 airline partners worldwide, so select the carrier that best suits your budget and traveling style.
If I'm not able to travel, can I cancel my Cheshire vacation package?
Don't worry if you're rethinking your Cheshire vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We totally understand life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Things to do

Asheville Hop-On Hop-Off Sightseeing Trolley Tour

Asheville Hop-On Hop-Off Sightseeing Trolley Tour

CA $56
per adult
80% of travellers recommend
Asheville Hop-On Hop-Off Sightseeing Trolley Tour
Blue Ridge Parkway Asheville Self-Guided Audio Tour

Blue Ridge Parkway Asheville Self-Guided Audio Tour

CA $14
per traveller
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.