Woolwine Vacations from $429

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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 $476, price is now $429 per person
$429
per person
Jul 1 - Jul 3
found 9 hours ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
9.4/10 Exceptional! (329 reviews)
Spacious and clean rooms with various amenities.

Reviewed on May 22, 2026

The Promissory Hotel

The Promissory Hotel

2 out of 5
Downtown Roanoke
Price was $567, price is now $482 per person
$482
per person
Jul 1 - Jul 3
found 9 hours ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
9.4/10 Exceptional! (73 reviews)
Beautiful stay! Nicely kept place.

Reviewed on May 22, 2026

The Lodge at Primland, Auberge Collection

The Lodge at Primland, Auberge Collection

5 out of 5
Price was $1,578, price is now $1,410 per person
$1,410
per person
Jul 1 - Jul 3
found 9 hours ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
9/10 Wonderful! (32 reviews)
The resort is an experience. The staff were helpful and genuine.

Reviewed on Nov 9, 2025

Country Inn & Suites by Radisson, Roanoke, VA

Country Inn & Suites by Radisson, Roanoke, VA

3 out of 5
Alpine Hills
Price was $545, price is now $493 per person
$493
per person
Jul 10 - Jul 12
found 8 hours ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
9.2/10 Wonderful! (2,224 reviews)
clean room and warm breakfast

Reviewed on May 25, 2026

The Lofts at Downtown Salem

The Lofts at Downtown Salem

3.5 out of 5
Price was $518, price is now $473 per person
$473
per person
Jul 1 - Jul 3
found 9 hours ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
9.6/10 Exceptional! (381 reviews)
Great room! Lots of character. Staff was very helpful.

Reviewed on May 21, 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
$994 nightly
The price is $1,116 total per night from Jun 21 to Jun 22
$1,116 total
Jun 21 - Jun 22
Total with taxes and fees
The Lodge at Primland, Auberge Collection
Hotel Floyd

Hotel Floyd

2 out of 5
300 Rick Lewis Way Floyd VA
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $146 total per night from May 31 to Jun 1
$146 total
May 31 - Jun 1
Total with taxes and fees
9.8/10 Exceptional! (518 reviews)
"We loved the Hotel Floyd. Everything about it was great!"

Reviewed on May 21, 2026

Hotel Floyd
Econo Lodge Martinsville

Econo Lodge Martinsville

2 out of 5
1755 Virginia Ave Martinsville VA
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $67 total per night from Jun 9 to Jun 10
$67 total
Jun 9 - Jun 10
Total with taxes and fees
6.4/10 (508 reviews)
"We stayed here just passing through. The beds were clean, though there were small cigarette burns on some of the sheets. The rooms were secure and the premises quiet on the Friday night we stayed. We rented 2 rooms and one of them appeared to have mildew on the vent in the bathroom. One of the rooms ..."

Reviewed on May 21, 2026

Econo Lodge Martinsville
See all 249 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 $429 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.