Woolwine Vacations from $1,084

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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 $1,157, price is now $1,084 per person
$1,084
per person
May 13 - May 15
found 11 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

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 $1,227, price is now $1,122 per person
$1,122
per person
May 13 - May 15
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
7.4/10 Good! (1,045 reviews)
Just an overnight stay as we landed at midnight. Room was clean and grounds tidy. Front desk staff kind and considerate. This is our go-to spot and we love it.

Reviewed on Apr 11, 2026

The Promissory Hotel

The Promissory Hotel

2 out of 5
Downtown Roanoke
Price was $1,427, price is now $1,331 per person
$1,331
per person
May 13 - May 15
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
9.6/10 Exceptional! (28 reviews)
Excellent location. They are working on signage. Enter on Campbell ave. Parking garage is walkable. Great price! Highly recommend.

Reviewed on Apr 4, 2026

Budget Inn By OYO Natural Bridge I-81

Budget Inn By OYO Natural Bridge I-81

2 out of 5
Price was $1,157, price is now $1,084 per person
$1,084
per person
May 13 - May 15
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
6.4/10 (361 reviews)
Great room. Easy online reservation. Friendly clerk.

Reviewed on Dec 17, 2025

Country Inn & Suites by Radisson, Roanoke, VA

Country Inn & Suites by Radisson, Roanoke, VA

3 out of 5
Alpine Hills
Price was $1,255, price is now $1,182 per person
$1,182
per person
May 13 - May 15
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Roanoke (ROA)
9.2/10 Wonderful! (2,143 reviews)
Very convenient location minutes off of I 81. Unit was very clean, hotel was well-maintained. The breakfast was fresh and plentiful . Coffee was excellent. Staff was very friendly and very helpful. Would recommend a stay here!

Reviewed on Apr 12, 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
$754 nightly
The price is $847 total per night from Apr 22 to Apr 23
$847 total
Apr 22 - Apr 23
Total with taxes and fees
9/10 Wonderful! (31 reviews)
Star gazing & wine tasting was amazing! Staff extremely helpful. Excellent food. Check into the activities available for each day of your stay BEFORE you get there. Book early since the number of people for each activity can be limited. Some activities only available certain days.

Reviewed on Mar 21, 2026

The Lodge at Primland, Auberge Collection
Comfort Inn Martinsville

Comfort Inn Martinsville

3 out of 5
378 Commonwealth Blvd W Martinsville VA
Fully refundable
$118 nightly
The price is $132 total per night from May 10 to May 11
$132 total
May 10 - May 11
Total with taxes and fees
6.8/10 (642 reviews)
Ok

Reviewed on Apr 12, 2026

Comfort Inn Martinsville
Hotel Floyd

Hotel Floyd

2 out of 5
300 Rick Lewis Way Floyd VA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Apr 14 to Apr 15
$133 total
Apr 14 - Apr 15
Total with taxes and fees
9.6/10 Exceptional! (504 reviews)
The room was clean, eclectic, had some older features, like mattress, bathroom fixtures, but it had a homey feel with interesting furniture pieces. Very comfortable.

Reviewed on Apr 4, 2026

Hotel Floyd
See all 243 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 $1,084 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.