Greenwood Vacations from $808
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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.
Little Mod Hotel at the University
Venable
$855
per person
Nov 24 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (389 reviews)
Cute hotel and great location for the university. Room was clean and staff were friendly. Free parking was hard to come by, but the garage option was also very convenient for a price.
Reviewed on Oct 14, 2026
Shenandoah Wilderness Traveler
$825
per person
Nov 24 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
8.8/10 Excellent! (121 reviews)
The property was much larger than expected and included a lake. Our cabin was tucked in the woods off of a one lane paved road, with good parking spaces. We had a few mosquitoes in our cabin, and also a spider that stayed in its upper corner of the bathroom. The beds and pillows in our two bedroom cabin were very comfortable. Most of the channels on the TV were a little out of focus and we were unable to mirror our phones on the TV, even through we had property internet connected. The breakfast in the main lodge was good and reasonably priced. Prices in the General Store were very reasonable compared to typical resorts. Looking forward to another stay at a future date.
Reviewed on Sep 30, 2026
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.
What to do in Greenwood
Blue Ridge Parkway Virginia Self-Guided Audio Tour
$13
per traveler
Greenwood Hotel Deals
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$80 nightly
$92 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (3,142 reviews)
"I had a really nice stay at the English Inn. The staff were super friendly and helpful. The room was clean, and the corridors were quiet. The hot breakfast was an added bonus after a late night. Everything looked well-maintained, and the touches of England were delightful, including the phone booth ..."
Reviewed on Oct 14, 2026
Omni Charlottesville Hotel
212 Ridge McIntire Rd Charlottesville VA
$167 nightly
$191 total
Nov 8 - Nov 9
Total with taxes and fees
Motel 6 Staunton, VA
96 Baker Lane Staunton VA
Fully refundableReserve now, pay when you stay
$63 nightly
$70 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,017 reviews)
"The room was a little dirty. Hairs left in the bath, what looks like toothpaste spit down the tile wall. The floors made my socks dark brown. There was a very strong, strange smell in the room. The beds were HARD. The staff that we dealt with were very helpful and friendly. The lobby was nice."
Reviewed on Oct 13, 2026
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 $808 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?
- 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.
- 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.
- 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.
- 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.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Greenwood vacation package for you.
- 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.
