Greenwood Vacations from $945

Book a Hotel + Flight or Car together to unlock savings

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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.
Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was $1,080, price is now $945 per person
$945
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Charlottesville (CHO)
9.2/10 Wonderful! (287 reviews)
A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $1,421, price is now $1,157 per person
$1,157
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Charlottesville (CHO)
8.6/10 Excellent! (907 reviews)
The hotel was minimal staff and self check in/out on line. For an old baby boomer I prefer a fully human staffed facility. Not sure I would have booked the hotel. Luckily I found a human in the lobby who helped me. When we left, the valet was nowhere to be found. Had to walk to the car. Hotel manager was unhappy and told me he would refund the parking cost. Have yet to see that money

Reviewed on Oct 12, 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,241, price is now $1,067 per person
$1,067
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Charlottesville (CHO)
9.2/10 Wonderful! (255 reviews)
Mod Pod foot truck on-site was an unexpected treat!

Reviewed on Oct 7, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,210, price is now $1,054 per person
$1,054
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Charlottesville (CHO)
9.2/10 Wonderful! (485 reviews)
Staff was so kind and the property was gorgeous. I travel for work and this was one of my favorite places I have stayed.

Reviewed on Sep 30, 2025

Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
Price was $1,325, price is now $1,158 per person
$1,158
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) to Charlottesville (CHO)
9.6/10 Exceptional! (375 reviews)
Wonderful hotel and restaurants for a football weekend!

Reviewed on Sep 28, 2025

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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

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

$24
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
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
$90 nightly
The price is $103 total per night from Nov 11 to Nov 12
$103 total
Nov 11 - Nov 12
Total with taxes and fees
9/10 Wonderful! (2,500 reviews)
"Lovely facility. Comfortable, clean, and located near lots of different shops."

Reviewed on Oct 7, 2025

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 Oct 16 to Oct 17
$70 total
Oct 16 - Oct 17
Total with taxes and fees
8.2/10 Very Good! (1,017 reviews)
"Every is ok"

Reviewed on Oct 12, 2025

Motel 6 Staunton, VA
DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

4 out of 5
990 Hilton Heights Rd, Charlottesville, VA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Oct 19 to Oct 20
$112 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
"Hotel was better than expected. Very beautiful inside and out."

Reviewed on Oct 7, 2025

DoubleTree by Hilton Hotel Charlottesville
See all 1,523 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.

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 $945 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.