Greenwood Vacations from $621

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Your Greenwood Vacation

Amazing adventures await when you reserve a vacation package to Greenwood. Whether you're a foodie, art buff or just a traveler who appreciates new places, there's something for everyone in this lively city. You'll want to do some exploring during your trip to Greenwood. Carve out some time for famous attractions like Veritas Vineyard and Winery, King Family Vineyards and Afton Mountain Vineyards. Don't delay exploring this city any longer. The perfect Greenwood vacation is just a few clicks away with Expedia.

The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $709, price is now $621 per person
$621
per person
Dec 9 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Weyers Cave (SHD)
8/10 Very Good! (1,634 reviews)

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Price was $745, price is now $654 per person
$654
per person
Dec 9 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Charlottesville (CHO)
9.8/10 Exceptional! (153 reviews)
Rooms

Reviewed on Oct 31, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $734, price is now $666 per person
$666
per person
Dec 9 - Dec 12
found 17 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,004 reviews)
We use this as a halfway stop between Maine and Florida twice a year. They are pet friendly and it’s just a mile off route 81 with good gas prices near the highway. The rooms are large with old wood floors, high ceilings and beautiful grounds around the hotel (which, I believe, used to be a sanitarium for people convalescing from tuberculosis). The beds and pillows are comfortable. They recently added a breakfast area though we haven’t tried it yet. The in room coffee only supplied a packet of powdered creamer and various sugar and sugar substitutes so we opted to get coffee locally instead.

Reviewed on Nov 1, 2026

Modern Peaks Hot Tub Sauna Theatre Room

Modern Peaks Hot Tub Sauna Theatre Room

2 out of 5
Price was $1,642, price is now $1,508 per person
$1,508
per person
Dec 9 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Weyers Cave (SHD)
No reviews

Afton Mountain Vineyards

Afton Mountain Vineyards

3.5 out of 5
Price was $1,112, price is now $1,026 per person
$1,026
per person
Dec 9 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Charlottesville (CHO)
7.4/10 Good! (3 reviews)

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Stay near popular Greenwood attractions

Pollak Vineyards

You can enjoy a tasting or tour at Pollak Vineyards during your travels to Greenwood. Discover the mountain views in this vibrant area.
See properties

What to do in Greenwood

Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

$13
per traveler
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Greenwood

Greenwood Hotel Deals

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $100 total per night from Nov 16 to Nov 17
$100 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (3,199 reviews)
"I liked how close it was to trails, the downtown and Barrack’s Row. The property had tea time with cookies and a very good breakfast.it was clean but a bit dated."

Reviewed on Nov 1, 2026

English Inn of Charlottesville
Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane Staunton VA
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $70 total per night from Nov 17 to Nov 18
$70 total
Nov 17 - Nov 18
Total with taxes and fees
8.2/10 Very Good! (1,037 reviews)
"The staff was wonderful. The room was outdated, but clean."

Reviewed on Nov 1, 2026

Motel 6 Staunton, VA
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
212 Ridge McIntire Rd Charlottesville VA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Nov 22 to Nov 23
$174 total
Nov 22 - Nov 23
Total with taxes and fees
9.6/10 Exceptional! (1,151 reviews)
"All good"

Reviewed on Nov 1, 2026

Omni Charlottesville Hotel
See all 1,665 properties in Greenwood
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 Greenwood Vacation Packages

Greenwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Veritas Vineyard and Winery, King Family Vineyards and Pippin Hill Farm & Vineyards

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Frequently asked questions

How much does a Greenwood vacation package cost?
You'll find cheap prices from $621 on Expedia for your Greenwood getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Greenwood costs.
What are the cheapest months to go to Greenwood?
You can usually find reduced prices and better availability in November, December and January. Browse our cheap Greenwood vacation packages and you could get some excellent off-season deals.
How many days is enough for Greenwood?
The ideal duration of your Greenwood vacation depends on what you'd like to do and see. Typically, a few days to a week will give you plenty of time to visit all the major sights and explore some hidden gems along the way.
How to find the best Greenwood package deals?
Use Expedia's filter tool to find some tempting Greenwood package deals. When you start your search, simply 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 Greenwood package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Greenwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a customized Greenwood vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Greenwood?
If you're considering an impromptu Greenwood vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Greenwood?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Greenwood.
  2. Budget wisely: Besides the price of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Greenwood.
  3. Discover Greenwood using Expedia's trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Greenwood. You can also save your must-visit places, collaborate with your group and organize your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Greenwood, you can figure out the right length of your vacation. Create a rough itinerary and give yourself enough time to get through everything on your must-do list.
  5. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Greenwood vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on Greenwood's highlights. Find all the incredible things to do in Greenwood with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
Jet off on your dream escape to Greenwood with our Book Now, Pay Later vacations. No need to save up or hold off until your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.