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.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
per person
Jul. 15 - Jul. 18
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
9/10 Wonderful! (1,678 reviews)
Very quiet, clean and a great breakfast

Reviewed on Jun. 3, 2024

Quirk Charlottesville

Quirk Charlottesville

3.5 out of 5
Starr Hill
per person
Jul. 15 - Jul. 18
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
9/10 Wonderful! (422 reviews)
This property was quaint, and the staff was excellent. I loved the rooftop restaurant.

Reviewed on May 15, 2024

Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
per person
Jul. 15 - Jul. 18
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
8.8/10 Excellent! (1,002 reviews)
Great location for walking. Beautiful bar and lounge area next to the lobby.

Reviewed on Jun. 5, 2024

Kimpton The Forum Hotel, an IHG Hotel

Kimpton The Forum Hotel, an IHG Hotel

4 out of 5
per person
Jul. 15 - Jul. 18
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
9.6/10 Exceptional! (182 reviews)
Great all round hotel.

Reviewed on Jun. 5, 2024

Boar's Head Resort

Boar's Head Resort

4 out of 5
Ednam
per person
Jul. 15 - Jul. 18
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
9/10 Wonderful! (943 reviews)
Very nice resort friendly and professional staff and very helpful overall very pleasant experience

Reviewed on May 16, 2024

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 $136 per night from Jul. 2 to Jul. 3
CA $136
CA $154 total
includes taxes & fees
Jul 2 - Jul 3
8.8/10 Excellent! (1,692 reviews)
"Very quiet, clean and a great breakfast"

Reviewed on Jun. 3, 2024

English Inn of Charlottesville
Sleep Inn Staunton
Sleep Inn Staunton
2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Jun. 9 to Jun. 10
CA $121
CA $135 total
includes taxes & fees
Jun 9 - Jun 10
9/10 Wonderful! (1,012 reviews)
"Room was clean & comfortable. Enjoyed the breakfast also"

Reviewed on Jun. 2, 2024

Sleep Inn Staunton
Days Inn by Wyndham Charlottesville/University Area
Days Inn by Wyndham Charlottesville/University Area
2 out of 5
1610 Emmet St N, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Jun. 16 to Jun. 17
CA $102
CA $116 total
includes taxes & fees
Jun 16 - Jun 17
7.4/10 Good! (1,005 reviews)
"Multiple hotels in area made parking tight and closeness of highway created all night noisiness. Room was decent although daily maid service was incomplete (bed not made)."

Reviewed on Jun. 4, 2024

Days Inn by Wyndham Charlottesville/University Area
See all 1,472 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Greenwood vacation package cost?
Custom build your Greenwood vacation package from only CA $568. Pick from any combination of flights, hotels and rental cars to build the getaway you’ve long been dreaming about. Be sure to add on some activities and experiences!
How do I get a cheap travel package to Greenwood?
Our Greenwood vacation packages offer plenty of savings for the savvy explorer. For the best deals, simply combine your flights, hotels and activities into an affordable package. But cheap prices are just the beginning of your next memorable adventure. Book with Expedia and you’ll have more than 550 air carriers and 1,000,000 hotel options around the globe to pick from. Whatever your style, there’s a package that’s perfect for you.
Where should I stay in Greenwood?
Greenwood has numerous top places to see, such as King Family Vineyards. Stay somewhere close by and make sightseeing stress-free.
What are the top hotels in Greenwood?
Secure a room at Ramsay Estate | Carriage House W. It’s one of the neighborhood’s most sought-after properties. Another well-known option in Greenwood is Gorgeous Farmhouse At Ramsay Estate | Amazing Blue Ridge Views.
How far in advance should I book my Greenwood vacation?
To land discount prices, book early. Air carriers usually release flight tickets, along with some of the lowest fares, up to 12 months prior to departure. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you’re in need of a last-minute getaway in Greenwood, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Greenwood travel package include?
It comes down to what you’re after. If you’re traveling alone, you might decide to bundle hotels and flights. Taking the whole family to Greenwood? A travel package that includes rental cars, flights and hotels might be a better fit. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a Greenwood travel package?
You’ll score excellent savings when you bundle your flights, hotels and rental cars into a package. Not only that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you’re putting together a ritzy romantic getaway or a budget solo adventure, browse our vacation packages today.
Can I choose my airline with a Greenwood Expedia vacation package?
Yes, and with over 550 airlines to choose from throughout the world, you have loads of choice. Search the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Greenwood vacation package?
Whether it’s your hotel, flight or rental car, you can cancel and rebook it. Booked your Greenwood vacation package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may incur a fee from your airline, hotel or car rental company. For further information, look up our Customer Service Portal. We’ll help you each step of the way.

Discover the most popular places to visit in Greenwood

Image for Pollak Vineyards

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

Image for Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen

Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen

CA $169
Per adult
Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen
Image for Blue Ridge Parkway Tour: Self-Guided Drive

Blue Ridge Parkway Tour: Self-Guided Drive

CA $30
Per adult
94% of travellers recommend
Blue Ridge Parkway Tour: Self-Guided Drive
Image for East Coast USA: Self-Guided Driving & Walking Tour Bundle

East Coast USA: Self-Guided Driving & Walking Tour Bundle

CA $102
Per adult
East Coast USA: Self-Guided Driving & Walking Tour Bundle
See all activities in Greenwood

Other vacations you might like

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