Greenwood Vacation Packages

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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.

Top Greenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Harrisonburg

Howard Johnson by Wyndham Harrisonburg

2 out of 5
per person
Sep 11 - Sep 18
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Weyers Cave (SHD)
6.8/10 (1,014 reviews)
Everything was good.

Reviewed on Jul. 29, 2025

Ramada by Wyndham Harrisonburg

Ramada by Wyndham Harrisonburg

2 out of 5
per person
Sep 11 - Sep 18
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Weyers Cave (SHD)
6.8/10 (1,004 reviews)
Excellent breakfast.

Reviewed on Jul. 8, 2025

Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

2 out of 5
per person
Sep 11 - Sep 18
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Weyers Cave (SHD)
7.2/10 Good! (1,001 reviews)
This was a low rate but in the future I would spend a bit more to stay at a motel nearby. The rooms smelled like cigarette smoke despite dire warnings not to smoke in the rooms. It is not fair to judge people on appearance but there looked to be some sketchy pople staying there.

Reviewed on Jul. 29, 2025

Days Inn by Wyndham Staunton

Days Inn by Wyndham Staunton

2 out of 5
per person
Sep 11 - Sep 18
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Weyers Cave (SHD)
7.4/10 Good! (1,007 reviews)
Clean. Good value for the price.

Reviewed on Jul. 10, 2025

Clarion Pointe Harrisonburg

Clarion Pointe Harrisonburg

2.5 out of 5
per person
Sep 11 - Sep 18
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Weyers Cave (SHD)
8.6/10 Excellent! (1,083 reviews)
The walls in this location are unfortunately thin. The first room I was given was next to a room that was blasting their TV. It was one in the morning. I went back and got a different room. It was all quiet until 6 AM when an alarm clock in the room next to me went off. It continued for nearly 30 minutes until I called the front desk. By that time, the damage was done, my kid was already awake, and there was no going back to sleep. Decent sheets and towels.

Reviewed on Aug. 2, 2025

Ready to book your vacation to Greenwood?

 

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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
The price is CA $126 per night from Aug 17 to Aug 18
CA $126
CA $149 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (2,371 reviews)
"There was one incident that has really bother me, the first morning there we went down for breakfast, we had just settle in when a black mean that was ing the food in a very loud voice said “mam”, tm got quiet no one moved or spoke this did’t satisfy. Nnjjji"

Reviewed on Aug. 1, 2025

English Inn of Charlottesville
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
The price is CA $135 per night from Aug 10 to Aug 11
CA $135
CA $154 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Good in the restaurant was awful, room was a bit dingy but overall clean. Lobby is very nice and staff was very nice. Overall would stay there again."

Reviewed on Jul. 31, 2025

DoubleTree by Hilton Hotel Charlottesville
Extended Stay America Premier Suites - Charlottesville

Extended Stay America Premier Suites - Charlottesville

2.5 out of 5
3400 Berkmar Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Aug 10 to Aug 11
CA $103
CA $118 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (157 reviews)
"Room was very clean and beds were very comfortable!! And big room! My only complaints are there was no soap or shampoo for shower just 1 small soap at sink. And no mirror in room just bathroom mirror! Next we could not get tv to work, it would only stay on the food network! Breakfast is virtually ..."

Reviewed on Aug. 2, 2025

Extended Stay America Premier Suites - Charlottesville
See all 1,466 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.
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What to do in Greenwood

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

CA $18
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $33
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
See all activities in Greenwood

Frequently asked questions

How much does a Greenwood vacation package cost?
Offering excellent value package deals from CA $907 on Expedia, you'll be surprised at how little a vacation to Greenwood costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Greenwood?
Plan your getaway for the low season and you're likely to find cheap Greenwood vacation packages. Remember that public holidays and major local events can have an impact on prices, so do a little research before booking.
How many days is enough for Greenwood?
To fully enjoy your Greenwood vacation, we suggest staying for 3 days. Divide your time between discovering Afton Mountain Vineyards, Valley Road Vineyards and other must-see attractions, as well as exploring neighbourhoods like Wayland Park and Western Ridge. If you've got some spare time, add a day trip or tour to your Greenwood vacation itinerary.
How to find the best Greenwood package deals?
Begin your search for a Greenwood package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Greenwood package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Greenwood escape underway.
Is it cheaper to book a Greenwood vacation as a package?
You can enjoy significant savings on your next Greenwood break by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Greenwood?
If you've got your Greenwood travel dates finalized, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Greenwood?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the available activities will also help you decide when to vacation in Greenwood.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your hotel will likely be the biggest expense during your trip to Greenwood.
  3. Work out your trip length: Consider how long you'd like to spend discovering Greenwood. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Greenwood vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.