Greenwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Greenwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG
$597
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
Book a stay at this golf hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Factory Antique Mall and Bertie Murphy Deming Fine Arts Center are located nearby.
Oakhurst Inn at the University
Jefferson Park Avenue
$735
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Virginia Guesthouse Hotel
Lewis Mountain
$811
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
The room and bathroom were spacious and clean. We ate dinner in the Poplar Restaurant. The food was excellent, and they gave us a free dessert for our anniversary.
Everything is brand new, and the staff was very helpful and kind.
Reviewed on Aug 30, 2026
The Doyle Hotel
Starr Hill
$773
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
To start, there was no valet when we arrived. They never cleaned rooms or brought towels. There appears to be no staff so it is very difficult to get assistance with things. Beds were comfy though.
Reviewed on Aug 30, 2026
Little Mod Hotel at the University
Venable
$706
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Shenandoah Wilderness Traveler
$600
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
Stay at this hotel in Gordonsville. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attraction Graves Fine Art Gallery is located nearby.
Awesome atmosphere, great place!
Reviewed on Aug 25, 2026
Top Hotel Deals
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
Omni Charlottesville Hotel
212 Ridge McIntire Rd Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and ...
Sleep Inn Staunton
222 Jefferson Hwy Staunton VA
Book a stay at this business-friendly hotel in Staunton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hotel 24 South
24 South Market Street Staunton VA
Book a stay at this historic hotel in Staunton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the convenient ...
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
1600 Emmet Street Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Hotel Charlottesville
990 Hilton Heights Rd Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Holiday Inn Charlottesville-Monticello by IHG
1200 5th St. SW Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Holiday Inn Charlottesville-Univ Area by IHG
1901 Emmet St N Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Days Inn by Wyndham Charlottesville/University Area
1610 Emmet St N Charlottesville VA
Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
The Blackburn Inn and Conference Center
301 Greenville Avenue Staunton VA
Stay at this hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
avid hotel Staunton by IHG
62 Sangers Lane Staunton VA
Book a stay at this business-friendly hotel in Staunton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Staunton Conference Center by IHG
152 Fairway Lane Staunton VA
Book a stay at this golf hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Comfort Inn & Suites Charlottesville Hollymead Town Center
1615 Timberwood Blvd Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express & Suites Charlottesville by IHG
870 PANTOPS CORNER WAY Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, a fitness center, and parking (surcharge). Our guests praise the breakfast ...
Holiday Inn Express & Suites Waynesboro East by IHG
108 Chicurel Lane Waynesboro VA
Stay at this hotel in Waynesboro. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Oct 6 - Tue, Oct 13
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$299
Roundtrip
found 6 days ago
Tue, Oct 20 - Sat, Oct 31
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$301
Roundtrip
found 4 days ago
Tue, Oct 20 - Sat, Oct 31
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$301
Roundtrip
found 4 days ago
Tue, Oct 20 - Sat, Oct 31
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$301
Roundtrip
found 4 days ago
Best points of interest in Greenwood
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations