Greenwood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Greenwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Harrisonburg
Price was CA $562, price is now CA $506 per person
CA $506
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Weyers Cave (SHD)
8.6/10 Excellent! (1,326 reviews)
We were greeted by a very friendly employee who checked us in. We didn't get to make any requests since we were told that every room was taken since there was a firefighters organization staying at the hotel. The room was small but was comfortable enough for one night. You could tell that this hotel had been another hotel and seemed rather old. We had a nice breakfast and the beds were comfortable.
Reviewed on May 9, 2026
Sleep Inn Staunton
Price was CA $653, price is now CA $533 per person
CA $533
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,440 reviews)
Well lit parking lot. Very accommodating staff. Comfortable beds. Complementary breakfast had a good selection.
Reviewed on May 8, 2026
Shenandoah Wilderness Traveler
Price was CA $618, price is now CA $553 per person
CA $553
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
8.8/10 Excellent! (86 reviews)
I loved everything about my stay here; comfortable and clean accommodations, beautiful grounds, an on-site stables with many lovely rescued horses, wonderful restaurant inside the lodge, and a very welcoming and helpful staff. I would definitely love to stay here again one day! Thank you, Shenandoah Wilderness Traveler, for making my stay so enjoyable!
Reviewed on May 4, 2026
Greenwood Hotel Deals
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jun 1 to Jun 2
CA $149
CA $175 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (2,825 reviews)
The room was spacious and had a comfortable bed, but twice we found long black hair that wasn’t ours on a pillow and the comforter. Our towels had rips in them. One of the bedside lamps had a burned out bulb, and when I went down to the desk to ask for a replacement, there was no one there for a ...
Reviewed on May 8, 2026
Omni Charlottesville Hotel
212 Ridge McIntire Rd Charlottesville VA
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from May 26 to May 27
CA $240
CA $274 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,028 reviews)
Very nice staff! Well located, indoor parking, nice bar/lounge, room was clean and nicely appointed, excellent breakfast.
Reviewed on May 6, 2026
Sleep Inn Staunton
222 Jefferson Hwy Staunton VA
Fully refundable
The price is CA $142 per night from May 17 to May 18
CA $142
CA $158 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (1,440 reviews)
Well lit parking lot. Very accommodating staff. Comfortable beds. Complementary breakfast had a good selection.
Reviewed on May 8, 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.
What to do in Greenwood
Blue Ridge Parkway Self-Guided Audio Tour Bundle
CA $33
per traveller
Shenandoah National Park Self-Guided Driving Audio Tour
CA $23
per traveller
100% of travellers recommend
Blue Ridge Parkway Virginia Self-Guided Audio Tour
CA $18
per traveller
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
