Upward Vacations from $625

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Your Upward Vacation

When you book a vacation package to Upward, you can relax and enjoy your break knowing that all your travel arrangements are in order. Discover the charms of this amazing city while based in a neighborhood like Hyman Heights Historic District, which is great for history. Flat Rock Playhouse, Carl Sandburg Home National Historic Site and Connemara are just some of the many sights you'll want to check out during your trip to Upward. Stop daydreaming and start doing. Explore the multitude of options on Expedia today and put your Upward vacation plans into action!

The Latest Upward vacation packages

Price found within the past 48 hours. Click for updated prices.
Fox Run at Lake Lure

Fox Run at Lake Lure

4.5 out of 5
Price was $774, price is now $625 per person
$625
per person
Jul 2 - Jul 5
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Asheville (AVL)
9.2/10 Wonderful! (201 reviews)
Clean rooms, a well-equipped kitchen, and a very relaxing atmosphere

Reviewed on May 4, 2026

The Restoration Asheville

The Restoration Asheville

4 out of 5
Downtown Asheville
Price was $1,456, price is now $1,127 per person
$1,127
per person
Jun 18 - Jun 22
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Asheville (AVL)
9.8/10 Exceptional! (1,229 reviews)
The hotel was fantastic! We loved how it was central to everything and all the bars it had onsite. We really like the breakfast baskets!

Reviewed on May 16, 2026

Kimpton Hotel Arras by IHG

Kimpton Hotel Arras by IHG

4 out of 5
Downtown Asheville
Price was $1,468, price is now $1,169 per person
$1,169
per person
Jun 18 - Jun 22
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Asheville (AVL)
9.6/10 Exceptional! (1,003 reviews)
From start to finish, this stay was everything we needed! Can’t wait to come back.

Reviewed on May 17, 2026

The Windsor Boutique Hotel

The Windsor Boutique Hotel

4 out of 5
Downtown Asheville
Price was $1,463, price is now $1,169 per person
$1,169
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Miami (MIA) to Asheville (AVL)
9.8/10 Exceptional! (592 reviews)
We absolutely loved our stay at the Windsor! The staff was friendly, the location was in the heart of downtown so shopping and food are walkable. The room was very clean and had everything you would need. Our room included a refrigerator, stove, microwave, washer,dryer, etc. It was a very cozy room that felt like a home away from home. If we are ever on the area again we will definitely be staying at the Windsor again!

Reviewed on May 16, 2026

The Radical Asheville, Tapestry Collection by Hilton

The Radical Asheville, Tapestry Collection by Hilton

4 out of 5
River Arts District
Price was $925, price is now $755 per person
$755
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Asheville (AVL)
9.6/10 Exceptional! (557 reviews)
Fun hotel with great roof top bar and fantastic coffee shop at After/Glow.

Reviewed on May 12, 2026

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Discover the most popular places to visit in Upward

Carl Sandburg Home National Historic Site

Carl Sandburg Home National Historic Site

4.5/5(13 reviews)

Find out about the history of Flat Rock with a stop at Carl Sandburg Home National Historic Site. Wander the lakeside or discover the area's mountain views.

Carl Sandburg Home National Historic Site
Carl Sandburg Home National Historic Site

Connemara

4/5(8 reviews)

You can find out about the history of Flat Rock when you stop by Connemara. Stroll along the lakeside or discover the area's mountain views.

Connemara

Flat Rock Playhouse

5/5(1 review)

Enjoy a show at Flat Rock Playhouse, a theater with a story to tell in Flat Rock. Discover the mountain views while you're in the area.

Flat Rock Playhouse

Upward Hotel Deals

The Lodge at Flat Rock

The Lodge at Flat Rock

3.5 out of 5
42 Mcmurray Rd Flat Rock NC
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $131 total per night from May 18 to May 19
$131 total
May 18 - May 19
Total with taxes and fees
9.8/10 Exceptional! (1,227 reviews)
My third stay. It was and has always been great. Friendly, safe, quiet, convenient. And my dog is always welcomed warmly😊.

Reviewed on May 6, 2026

The Lodge at Flat Rock
Hampton Inn Hendersonville

Hampton Inn Hendersonville

2.5 out of 5
155 Sugarloaf Rd Hendersonville NC
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $119 total per night from May 24 to May 25
$119 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (1,017 reviews)
Nice, clean room with comfy bed and bedding. Good breakfast with friendly staff.

Reviewed on May 15, 2026

Hampton Inn Hendersonville
Wingate by Wyndham Fletcher at Asheville Airport

Wingate by Wyndham Fletcher at Asheville Airport

3 out of 5
31 Airport Park Rd Fletcher NC
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from May 28 to May 29
$98 total
May 28 - May 29
Total with taxes and fees
8.6/10 Excellent! (1,210 reviews)
Stayed in room 137. It was nice clean and quiet but the shower, no matter how careful you are, floods the entire bathroom floor.

Reviewed on May 16, 2026

Wingate by Wyndham Fletcher at Asheville Airport
See all 2,943 properties in Upward
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.

Find the Best Upward Vacation Packages

Upward Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Greenville-Spartanburg Intl. Airport (GSP)
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Flat Rock Playhouse, Carl Sandburg Home National Historic Site and Connemara

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Frequently asked questions

How much does an Upward vacation package cost?
Offering excellent value package deals from $625 on Expedia, you'll be surprised at how little a vacation to Upward costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Upward?
You can typically find reduced prices and better availability in June, November and December. Take a look at our cheap Upward vacation packages and you could get some excellent off-season deals.
How many days is enough for Upward?
With a well-organized travel plan, you can easily hit the top Upward sights in a few days. But if you'd like to discover hidden gems or take day trips, consider booking your Upward vacation for longer.
How to find the best Upward package deals?
Begin your search for an Upward package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Upward package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Upward escape underway.
Is it cheaper to book an Upward vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Upward vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Upward?
If you're considering a spur-of-the-moment Upward adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Upward vacation packages?
Secure your dream getaway to Upward with help from our Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up cheap deals before they sell out.

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