Woolwine Vacations from $596

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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.
Affordable Corporate Suites of Overland Drive

Affordable Corporate Suites of Overland Drive

2.5 out of 5
Price was $634, price is now $596 per person
$596
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Roanoke (ROA)
9.4/10 Exceptional! (314 reviews)
Nice place to stay. Everything needed was already there. Property manager was kind and very helpful.

Reviewed on Mar 2, 2026

The Omni Homestead Resort & Spa

The Omni Homestead Resort & Spa

4 out of 5
Price was $1,409, price is now $1,183 per person
$1,183
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
8.6/10 Excellent! (1,000 reviews)
Great time with the family!

Reviewed on Mar 5, 2026

Hotel Red Rose by Townhouse Covington I-64

Hotel Red Rose by Townhouse Covington I-64

2.5 out of 5
Price was $712, price is now $634 per person
$634
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
5.8/10 (445 reviews)
Room was fine. Amenities wasn’t great.

Reviewed on Nov 28, 2025

The Promissory Hotel

The Promissory Hotel

2 out of 5
Downtown Roanoke
Price was $738, price is now $661 per person
$661
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Roanoke (ROA)
9.6/10 Exceptional! (10 reviews)
The staff were great and the room was beautiful and spacious!

Reviewed on Mar 1, 2026

The Liberty Trust

The Liberty Trust

4 out of 5
Downtown Roanoke
Price was $719, price is now $679 per person
$679
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Roanoke (ROA)
9.2/10 Wonderful! (1,303 reviews)
The HVAC was loud in the room and blew either super cold or hot. It's a neat hotel, that has charm, but not really worth the hype. The restaurant for dinner is super limited menu, nothing great on it either.

Reviewed on Mar 6, 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 15 to Mar 16
$758 total
Mar 15 - Mar 16
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
$111 nightly
The price is $124 total per night from Mar 15 to Mar 16
$124 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
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 Mar 8 to Mar 9
$133 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (497 reviews)
Clean room, the room was decorated with items from local artisans. Walking distance to restaurants.

Reviewed on Mar 5, 2026

Hotel Floyd
See all 242 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 $596 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.