Greenwood Vacations from $811

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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.

Virginia Guesthouse At University Of Virginia

2 out of 5
Lewis Mountain
Price was $1,156, price is now $811 per person
$811
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
No reviews
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,248, price is now $963 per person
$963
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
9.6/10 Exceptional! (320 reviews)
Staff and service was amazing. The room was huge and charming with a four poster bed and a separate claw foot tub and glass shower.

Reviewed on Feb 4, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,284, price is now $998 per person
$998
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Our room was clean and the staff was super friendly and courteous. We did hope that our room had a microwave and refrigerator. It makes sense to have that available in every room on the grounds. Guests I’m sure would appreciate it. Please consider doing this. Lastly, we could here noises above us from possibly furniture that wasn’t secure. Footsteps are understandable, but the rattle of something above room 5 was a bit annoying. This is probably an eat fix. Overall the property was safe, clean and convenient.

Reviewed on Jan 1, 2026

Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Venable
Price was $1,249, price is now $1,004 per person
$1,004
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
8.2/10 Very Good! (1,001 reviews)
Love this hotel! Everyone—and I mean everyone—was super friendly and welcoming. The room was cozy and comfortable. Best of all, you really cannot beat the location!

Reviewed on Jan 30, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $1,085, price is now $874 per person
$874
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Charlottesville (CHO)
8.6/10 Excellent! (944 reviews)
Everything was perfect 5 stars no doubt.

Reviewed on Jan 27, 2026

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Discover the most popular places to visit in Greenwood

Great wine and great people. Cheers.

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.

Pollak Vineyards

What to do in Greenwood

Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$16
per traveler
Shenandoah National Park Self-Guided Audio Tour
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
$89 nightly
The price is $102 total per night from Feb 25 to Feb 26
$102 total
Feb 25 - Feb 26
Total with taxes and fees
9.2/10 Wonderful! (2,709 reviews)
Clean rooms, quiet facility, immaculate pool.

Reviewed on Jan 29, 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
$151 nightly
The price is $173 total per night from Feb 8 to Feb 9
$173 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Perfect

Reviewed on Feb 2, 2026

Omni Charlottesville Hotel
Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
1309 W Main St Charlottesville VA
Fully refundable
$104 nightly
The price is $119 total per night from Feb 12 to Feb 13
$119 total
Feb 12 - Feb 13
Total with taxes and fees
8.8/10 Excellent! (27 reviews)
Love this hotel! Everyone—and I mean everyone—was super friendly and welcoming. The room was cozy and comfortable. Best of all, you really cannot beat the location!

Reviewed on Jan 30, 2026

Graduate by Hilton Charlottesville
See all 1,597 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 $811 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.