Stuart Vacations from $374

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Your Stuart Vacation

There's no better way to escape than with one of our vacation packages to Stuart. The rich history and spectacular views are two of the many reasons to stay in this captivating city. There's plenty to add to your must-see list during a trip to Stuart, beginning with leading sights such as Wood Brothers Racing Museum and Stanburn Winery. Expedia is here to help you escape your routine. Tailor your vacation to Stuart to suit your travel style, whatever that may be!

The Latest Stuart vacation packages

Price found within the past 48 hours. Click for updated prices.
Relax Inn By OYO Natural Bridge I-81

Relax Inn By OYO Natural Bridge I-81

2 out of 5
Price was $453, price is now $374 per person
$374
per person
May 15 - May 18
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
5.6/10 (159 reviews)
The place is very close to the natural bridge, (4mi) and close enough to Lexington as well. The rooms are a bit dated, the bed had a burn mark (non smoking room...?) and it allows pets. The room next door had a dog that kept barking every time I moved around my room. There are probably better options out there.

Reviewed on Sep 7, 2025

The West End Flats

The West End Flats

4.5 out of 5
West End
Price was $630, price is now $508 per person
$508
per person
May 15 - May 18
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
9.4/10 Exceptional! (98 reviews)
We didn't see any staff and the room was still a bit dirty, but finding the room was straightforward and they provided all the necessary information.

Reviewed on Jan 19, 2026

Days Inn by Wyndham Roanoke/Hollins Near I-81

Days Inn by Wyndham Roanoke/Hollins Near I-81

2 out of 5
Alpine Hills
Price was $534, price is now $437 per person
$437
per person
May 15 - May 18
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
7.4/10 Good! (1,021 reviews)
Room was clean and decent breakfast.

Reviewed on Feb 24, 2026

The Promissory Hotel

The Promissory Hotel

2 out of 5
Downtown Roanoke
Price was $779, price is now $647 per person
$647
per person
May 15 - May 18
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
9.6/10 Exceptional! (10 reviews)
Lovely stay I would be back

Reviewed on Mar 7, 2026

Holiday Inn Roanoke-Tanglewood-Rt 419&i581 by IHG

Holiday Inn Roanoke-Tanglewood-Rt 419&i581 by IHG

3 out of 5
Price was $638, price is now $531 per person
$531
per person
May 15 - May 18
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
7.8/10 Good! (776 reviews)
Great front desk service . Fast check in. No concerns

Reviewed on Jan 28, 2026

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Discover the most popular places to visit in Stuart

Fairy Stone State Park

4.5/5(12 reviews)

You can take time to visit Fairy Stone State Park during your travels to Reserve at Fairystone. Amble around the area's parks or visit its churches.

Fairy Stone State Park

Lovers Leap Scenic Overlook

Explore the great outdoors at Lovers Leap Scenic Overlook, a lovely green space in Stuart. Discover the mountain views in this family-friendly area.

Lovers Leap Scenic Overlook

Wood Brothers Racing Museum

You can spend an afternoon exploring the galleries in Wood Brothers Racing Museum during your trip to Smith River. Discover the mountain views while you're in the area.

Wood Brothers Racing Museum

Stuart Hotel Deals

Secluded Romantic Escape near Fairy Stone State Park, Virginia

Secluded Romantic Escape near Fairy Stone State Park, Virginia

Stuart VA
10/10 Exceptional! (47 reviews)
This cabin was perfect! So peaceful with an amazing view. Everything was clean and updated. We had all the kitchen supplies we needed. 10 minutes from fairy stone state park for a few hiking trails. Greg is a great communicator. We would love to return!

Reviewed on Feb 15, 2026

Get rates
Secluded Romantic Escape near Fairy Stone State Park, Virginia
Virginian Motel

Virginian Motel

2 out of 5
105 W. Blue Ridge Street Stuart VA
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $69 total per night from Mar 31 to Apr 1
$69 total
Mar 31 - Apr 1
Total with taxes and fees
Virginian Motel
Cozy Cabin at The Reserve near Fairystone State Park

Cozy Cabin at The Reserve near Fairystone State Park

Stuart VA
$296 nightly
The price is $333 total per night from Mar 8 to Mar 9
$333 total
Mar 8 - Mar 9
Total with taxes and fees
9.8/10 Exceptional! (46 reviews)
Host was quick to respond with questions! Beautiful cabin with a unique floor plan. Especially enjoyed the back porch with gas fire pit!

Reviewed on Nov 25, 2025

Cozy Cabin at The Reserve near Fairystone State Park
See all 449 properties in Stuart
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 Stuart Vacation Packages

Stuart Essential Information

Language
English
Currency
U.S dollars
Population
1,450
Max Temp Winter
45ºF
Max Temp Summer
90ºF
Top Sights
Lovers Leap Scenic Overlook, Wood Brothers Racing Museum and Stanburn Winery

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Frequently asked questions

How much does a Stuart vacation package cost?
You'll find cheap prices from $374 on Expedia for your Stuart getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Stuart costs.
What are the cheapest months to go to Stuart?
If you're hoping to snag a cheap Stuart vacation package, consider traveling in March, August and December. You'll typically find lower prices on flights and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Stuart?
The ideal length of your Stuart vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to tick off all the main attractions and explore some hidden gems along the way.
How to find the best Stuart package deals?
Start your search for a Stuart package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Stuart package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Stuart getaway off to a flying start.
Is it cheaper to book a Stuart vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still have the freedom to create a tailored Stuart vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Stuart?
Land incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Stuart vacation.
Does Expedia offer Book Now, Pay Later Stuart vacation packages?
Set off on your ideal getaway to Stuart with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.