Upward Vacations from $509

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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.
The Restoration Asheville

The Restoration Asheville

4 out of 5
Downtown Asheville
Price was $746, price is now $509 per person
$509
per person
Mar 30 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.8/10 Exceptional! (984 reviews)
It was all wonderful!

Reviewed on Feb 8, 2026

The Windsor Boutique Hotel

The Windsor Boutique Hotel

4 out of 5
Downtown Asheville
Price was $838, price is now $636 per person
$636
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.8/10 Exceptional! (543 reviews)
Awesome! Erica was so helpful friendly and kind! We are going to go back in May!

Reviewed on Feb 7, 2026

The Foundry Hotel Asheville, Curio Collection by Hilton

The Foundry Hotel Asheville, Curio Collection by Hilton

4 out of 5
Downtown Asheville
Price was $738, price is now $574 per person
$574
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.2/10 Wonderful! (462 reviews)
Clean, quiet room. Good location.

Reviewed on Jan 23, 2026

Grand Bohemian Lodge Asheville, Autograph Collection®

Grand Bohemian Lodge Asheville, Autograph Collection®

4.5 out of 5
Biltmore Village
Price was $983, price is now $774 per person
$774
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.2/10 Wonderful! (890 reviews)
Luxury room and very friendly staff

Reviewed on Feb 13, 2026

The Omni Grove Park Inn & Spa

The Omni Grove Park Inn & Spa

4 out of 5
Grove Park- Sunset
Price was $938, price is now $750 per person
$750
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Asheville (AVL)
9.2/10 Wonderful! (1,003 reviews)
Staff was very friendly and helpful. They seemed to really care about providing a nice experience.

Reviewed on Feb 13, 2026

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Discover the most popular places to visit in Upward

The builder and first owner of the home was a wealthy slave owner who built the home in 1838 so that he and his family could escape the heat, yellow fever and malaria of the Charleston area. These buildings were originally slave quarters. Carl Sandburg turned them into outbuildings and guest cabins.

Carl Sandburg Home National Historic Site

4.5/5(12 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

Wingate by Wyndham Fletcher at Asheville Airport

Wingate by Wyndham Fletcher at Asheville Airport

2.5 out of 5
31 Airport Park Rd Fletcher NC
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $81 total per night from Feb 28 to Mar 1
$81 total
Feb 28 - Mar 1
Total with taxes and fees
8.6/10 Excellent! (1,164 reviews)
Room was nice ..staff was courteous and very helpful... amenities were great, nice size refrigerator.. microwave in room..bed was comfortable

Reviewed on Feb 5, 2026

Wingate by Wyndham Fletcher at Asheville Airport
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
$108 nightly
The price is $122 total per night from Feb 22 to Feb 23
$122 total
Feb 22 - Feb 23
Total with taxes and fees
9.6/10 Exceptional! (1,188 reviews)
Always the best,clean and comfortable. Great staff,and this property takes hospitality to a whole new level.From having welcome back on key card holder to a box of chocolates in the room.Not to mentioned complimentary water bottles and snacks in our room Location is convenient to interstate and restaurants ...

Reviewed on Feb 8, 2026

The Lodge at Flat Rock
Quality Inn & Suites Hendersonville - Flat Rock

Quality Inn & Suites Hendersonville - Flat Rock

2.5 out of 5
111 Commercial Boulevard Flat Rock NC
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $75 total per night from Feb 22 to Feb 23
$75 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Only one night, but cozy hotel. Very clean, quiet and staff very friendly!

Reviewed on Jan 29, 2026

Quality Inn & Suites Hendersonville - Flat Rock
See all 2,834 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 $509 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.