Greenwood Holidays from £441

Book a Hotel + Flight or Car together to unlock savings

Photo by Karyn Leary

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to £335 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages with flights are ATOL protected

Your Greenwood Holiday

Amazing adventures await when you reserve a holiday package to Greenwood. Whether you're a foodie, art buff or just a traveller 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 holiday is just a few clicks away with Expedia.

The Latest Greenwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Charlottesville-Univ Area by IHG

Holiday Inn Charlottesville-Univ Area by IHG

3 out of 5
The Meadows
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
7.8/10 Good! (1,005 reviews)
The hotel w spacious and also l clean only suggestion is t

Reviewed on 26 Jun 2025

Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
9/10 Wonderful! (1,005 reviews)
This was a pleasant surprise! Lovely hotel, exceptional staff and the conservatory is such a pleasant departure from the usual hotel lobby. Beautiful! We will come back!

Reviewed on 29 Jun 2025

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
9.4/10 Exceptional! (273 reviews)
great Breakfast included in stay. Very clean and a great deal of history.

Reviewed on 22 May 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
9.2/10 Wonderful! (224 reviews)
Just really well done and cozy!

Reviewed on 23 Jun 2025

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
9.2/10 Wonderful! (2,264 reviews)
Solid place to stay in Charlottesville. The property is aging but it’s got a pool and small gym and it’s close to UVA.

Reviewed on 29 Jun 2025

Comfort Inn Monticello

Comfort Inn Monticello

2.5 out of 5
per person
8 Aug - 11 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Charlottesville (CHO)
7.8/10 Good! (1,000 reviews)
Large hotel with no signs directing you to room numbers

Reviewed on 28 Jun 2025

Greenwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Veritas Vineyard and Winery, Pippin Hill Farm & Vineyards and King Family Vineyards

Our pick of the best Greenwood Hotel Deals

English Inn of Charlottesville
English Inn of Charlottesville
3 out of 5
2000 Morton Drive, Charlottesville, VA
Stay at this 3-star business-friendly hotel in Charlottesville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (2,268 reviews)
"Roomy, clean rooms. Great breakfast. Great location."

Reviewed on 26 Jun 2025

English Inn of Charlottesville
Omni Charlottesville Hotel
Omni Charlottesville Hotel
4 out of 5
212 Ridge McIntire Rd, Charlottesville, VA
Stay at this 4-star business-friendly hotel in Charlottesville. Enjoy free parking, an outdoor pool and 2 restaurants. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,002 reviews)
"Great location well maintained beautiful facility."

Reviewed on 25 Jun 2025

Omni Charlottesville Hotel
Sleep Inn Staunton
Sleep Inn Staunton
2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Stay at this business-friendly hotel in Staunton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
9.2/10 Wonderful! (1,184 reviews)
"like it"

Reviewed on 27 Jun 2025

Sleep Inn Staunton
See all 1,464 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Greenwood travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Greenwood from just £441. And the more you bundle, the more you save. The holiday of your dreams has never been so affordable.
If I'm not able to travel, can I cancel my Greenwood travel package?
Whether it's your hotel or flight, you can cancel or amend it. Locked in your Greenwood travel package in the last 24 hours? You may be able to make changes for free. If it's been longer than that, you may incur a charge from your airline, hotel or car rental company. For further information, look up our Customer Service Portal. We're here to help you each step of the way.
How do I get a cheap travel package to Greenwood?
Browse and book everything all in one place with our Greenwood travel packages. You'll find bargains on flights, hotels and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotels globally to choose from, you'll have the flexibility to mix and match as you please.
Does Expedia offer Book Now, Pay Later Greenwood holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's easy monthly instalment plans. If paying bite-sized amounts each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you spot an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Greenwood?
There's so much to do in Greenwood, so spend your evenings close to its attractions and spend more time sightseeing. King Family Vineyards is one place that should be on your itinerary.
What are the top hotels in Greenwood?
Hilton Holiday Club The Historic Powhatan Williamsburg and Best Western Potomac Mills are two of the most popular hotels in Greenwood. Why not look up the amenities and rates at each and then make up your mind?
How far in advance should I book my Greenwood holiday?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Many international journeys on Expedia become available to compare up to a year in advance. If you're booking last minute, fear not. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Greenwood travel package include?
Expedia has all you need to plan your Greenwood trip, but what your package looks like is your call. Select from any combination of rental cars, flights and hotels. After some tours or activities to keep you entertained? Once you've made your booking, you can add them on too. Whatever your budget, there's a deal to match your needs.
What should I know before booking a Greenwood travel package?
Our prices are always low. However, you'll score an even better deal when you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Greenwood Expedia travel package?
Yes, the choice is yours. We have access to over 550 airlines globally, so you can design your Greenwood holiday according to your travel preferences.

Unmissable things to do in Greenwood

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

£18
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

£10
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

£11
per traveller
Shenandoah National Park Self-Guided Audio Tour
See all activities in Greenwood

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.