Greenwood Vacations from $702

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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.
Motel 6 Harrisonburg, VA - South

Motel 6 Harrisonburg, VA - South

2 out of 5
Price was $769, price is now $702 per person
$702
per person
Jul 29 - Aug 4
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Weyers Cave (SHD)
7.2/10 Good! (984 reviews)
This was a perfect spot to stop with a very large moving truck and car dolly. Convenient to the highway, and has a Cracker Barrell next door. It is my understanding that there are some renovations going on, so it would be unfair to judge cleanliness of the property to harshly. The room and beds had some pet hair. Overall the stay was just what the weary traveler needed.

Reviewed on Jun 26, 2026

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $1,291, price is now $1,126 per person
$1,126
per person
Jul 29 - Aug 4
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Weyers Cave (SHD)
9/10 Wonderful! (382 reviews)
Great place to stay and lots to do.

Reviewed on Jun 25, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $951, price is now $851 per person
$851
per person
Jul 29 - Aug 4
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,008 reviews)
Room was a bit stuffy; to mediate it we were given a strange device which blew out cold air when ice was placed in it.

Reviewed on Jun 21, 2026

Best Western Plus Waynesboro Inn & Suites Conference Center

Best Western Plus Waynesboro Inn & Suites Conference Center

2.5 out of 5
Price was $1,019, price is now $917 per person
$917
per person
Jul 29 - Aug 4
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Weyers Cave (SHD)
8.6/10 Excellent! (1,006 reviews)
Only ding was the pool was closed. Good buffet breakfast. Friendly staff. Great location. Plenty of restaurants within walking distance. I didn’t know Cracker Barrel served alcohol. I do now. Good to have a cold one after traveling.

Reviewed on Jun 11, 2026

Best Western Plus Crossroads Inn & Suites

Best Western Plus Crossroads Inn & Suites

2.5 out of 5
Price was $1,151, price is now $1,042 per person
$1,042
per person
Sep 2 - Sep 7
found 6 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Charlottesville (CHO)
8.8/10 Excellent! (690 reviews)
The staff was great. The room was clean and the hot tub was awesome.

Reviewed on Jun 22, 2026

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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 $101 total per night from Jul 26 to Jul 27
$101 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (2,914 reviews)
"The unique architecture of the bldg inside & outside. Reminded us of when we lived in Germany."

Reviewed on Jun 27, 2026

English Inn of Charlottesville
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
212 Ridge McIntire Rd Charlottesville VA
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $170 total per night from Jul 7 to Jul 8
$170 total
Jul 7 - Jul 8
Total with taxes and fees
9.4/10 Exceptional! (1,047 reviews)
"Fantastic location- right on the mall with access to great shops and restaurants."

Reviewed on Jun 27, 2026

Omni Charlottesville Hotel
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Jul 12 to Jul 13
$114 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (1,175 reviews)
"Beautiful property and great little town for an overnight stay."

Reviewed on Jun 27, 2026

Hotel 24 South
See all 1,687 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 $702 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.