Woolwine Vacations from $374

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Your Woolwine Vacation

With a Woolwine vacation package, say goodbye to endless planning and hello to stress-free adventure. Every detail of your escape has been taken care of before you go, so you can get on with discovering this vibrant city. Lovers Leap Scenic Overlook and Fred Clifton Park are a couple of the major attractions to explore during your trip to Woolwine. Don't delay visiting this city any longer. The perfect Woolwine vacation is a couple of clicks away with Expedia.

The Latest Woolwine 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 1 day 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 1 day 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 1 day 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 1 day ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
9.8/10 Exceptional! (12 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 1 day ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
7.8/10 Good! (805 reviews)
Great front desk service . Fast check in. No concerns

Reviewed on Jan 28, 2026

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Woolwine Hotel Deals

The Lodge at Primland, Auberge Collection

The Lodge at Primland, Auberge Collection

5 out of 5
2000 Busted Rock Rd Meadows Of Dan VA
$675 nightly
The price is $758 total per night from Mar 18 to Mar 19
$758 total
Mar 18 - Mar 19
Total with taxes and fees
9.2/10 Wonderful! (28 reviews)
They loved my dog Stella, giving her homemade treats and a cute bandana! Very welcoming everywhere at the property including the formal dining room, she was complimented the entire time on her exemplary behavior. The staff here is second to none, the room stunning as well as the lodge and the views. ...

Reviewed on Mar 7, 2026

The Lodge at Primland, Auberge Collection
Comfort Inn Martinsville

Comfort Inn Martinsville

3 out of 5
378 Commonwealth Blvd W Martinsville VA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from Mar 15 to Mar 16
$122 total
Mar 15 - Mar 16
Total with taxes and fees
6.8/10 (631 reviews)
Such kind service and large variety for breakfast! Our sports team had a lovely stay here

Reviewed on Mar 1, 2026

Comfort Inn Martinsville
Scottish Inns Collinsville-Martinville

Scottish Inns Collinsville-Martinville

2 out of 5
2357 Virginia Ave Collinsville VA
Fully refundableReserve now, pay when you stay
$52 nightly
The price is $58 total per night from Mar 10 to Mar 11
$58 total
Mar 10 - Mar 11
Total with taxes and fees
6.8/10 (285 reviews)
This place is run down and very low end. It’s cheap for a reason, but in this case it isn’t even worth the $60 a night. I’d rather be camping outside. Our room smelled like a wet dog, the shower barely worked, the cold water side of the sink faucet didn’t work, the wall mounted heater was really ...

Reviewed on Mar 5, 2026

Scottish Inns Collinsville-Martinville
See all 240 properties in Woolwine
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 Woolwine Vacation Packages

Woolwine Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Fairy Stone State Park, Lovers Leap Scenic Overlook and Wood Brothers Racing Museum

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Frequently asked questions

How much does a Woolwine vacation package cost?
Offering excellent value package deals from $374 on Expedia, you'll be thrilled with how little a vacation to Woolwine costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woolwine?
March, August and December are great times to look for cheap Woolwine vacation packages. Traveling in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Woolwine?
Typically, a handful of days is enough to check out the top attractions during your Woolwine vacation. But if you'd like to have time to kick back or take day tours, consider extending your itinerary.
How to find the best Woolwine package deals?
Use Expedia's filters to help you find some terrific Woolwine package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Woolwine package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Woolwine vacation as a package?
You can enjoy significant savings on your next Woolwine break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Woolwine?
If you're considering an impromptu Woolwine getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Woolwine vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Woolwine vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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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.