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Wintergreen

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Wintergreen Flights as Low as $398

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$398 Roundtrip, just found
$398
Roundtrip
just found
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $398 just found
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$408 Roundtrip, found 7 hours ago
$408
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $408 found 7 hours ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $408 found 1 day ago
American Airlines
Wed, Sep 24 - Tue, Sep 30
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$410 Roundtrip, found 4 hours ago
$410
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 24 from Logan Intl. to Shenandoah Valley Regional, returning Tue, Sep 30, priced at $410 found 4 hours ago
United
Wed, Sep 24 - Tue, Sep 30
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$413 Roundtrip, found 4 hours ago
$413
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Sep 24 from Logan Intl. to Shenandoah Valley Regional, returning Tue, Sep 30, priced at $413 found 4 hours ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $418 found 1 day ago
American Airlines
Sat, Sep 27 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$418 Roundtrip, found 22 hours ago
$418
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $418 found 22 hours ago
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$420 Roundtrip, just found
$420
Roundtrip
just found
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $420 just found
American Airlines
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$420 Roundtrip, found 2 days ago
$420
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $420 found 2 days ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$422 Roundtrip, found 22 hours ago
$422
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $422 found 22 hours ago
United
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$423 Roundtrip, found 1 day ago
$423
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $423 found 1 day ago
United
Wed, Sep 24 - Tue, Sep 30
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$425 Roundtrip, found 4 hours ago
$425
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Sep 24 from Logan Intl. to Shenandoah Valley Regional, returning Tue, Sep 30, priced at $425 found 4 hours ago
American Airlines
Sun, Jul 27 - Tue, Jul 29
BWI
Baltimore Washington Intl. Thurgood Marshall
SHD
Shenandoah Valley Regional
$625 Roundtrip, found 1 day ago
$625
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jul 27 from Baltimore Washington Intl. Thurgood Marshall to Shenandoah Valley Regional, returning Tue, Jul 29, priced at $625 found 1 day ago
Delta
Wed, Jul 23 - Tue, Jul 29
BWI
Baltimore Washington Intl. Thurgood Marshall
CHO
Charlottesville-Albemarle
$894 Roundtrip, found 1 day ago
$894
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 23 from Baltimore Washington Intl. Thurgood Marshall to Charlottesville-Albemarle, returning Tue, Jul 29, priced at $894 found 1 day ago
American Airlines
Sat, Jul 26 - Wed, Jul 30
BWI
Baltimore Washington Intl. Thurgood Marshall
CHO
Charlottesville-Albemarle
$907 Roundtrip, found 1 day ago
$907
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 26 from Baltimore Washington Intl. Thurgood Marshall to Charlottesville-Albemarle, returning Wed, Jul 30, priced at $907 found 1 day ago
United
Thu, Jul 24 - Sun, Jul 27
BWI
Baltimore Washington Intl. Thurgood Marshall
CHO
Charlottesville-Albemarle
$1,147 Roundtrip, found 1 day ago
$1,147
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jul 24 from Baltimore Washington Intl. Thurgood Marshall to Charlottesville-Albemarle, returning Sun, Jul 27, priced at $1,147 found 1 day ago

Cheap Flights to Wintergreen

Fall in love at first flight with your vacation to Wintergreen by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Wintergreen on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Wintergreen, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Wintergreen

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Wintergreen with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHO airport.

What is the cheapest month to fly to Wintergreen?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Wintergreen are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Wintergreen?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Wintergreen.

What airport is best to fly into Wintergreen?

When you’re planning your trip to Wintergreen, convenience is the name of the game. Luckily, Wintergreen Shenandoah Valley Regional Airport is nearby so you can deplane and get going on checking off everything on your Wintergreen must-do list.

How much are flights to Wintergreen?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Wintergreen on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $398, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Wintergreen?

The trick to saving a stack of cash on your flight to Wintergreen? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $398 right now, why wait?

Wintergreen Flight Information
Destination airport
Charlottesville-Albemarle
Destination airport IATA code
CHO
Roundtrip price
$179

Last Minute Hotel Deals in Wintergreen

Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
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 ...
9.2/10 Wonderful! (1,216 reviews)
"Would stay again"

Reviewed on Jul 17, 2025

Get rates
Sleep Inn Staunton
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street, Staunton, VA
Stay at this 3-star historic hotel in Staunton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the convenient ...
9.4/10 Exceptional! (1,008 reviews)
"Great property. Great location. Love the town."

Reviewed on Jul 18, 2025

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Hotel 24 South
Howard Johnson by Wyndham Staunton

Howard Johnson by Wyndham Staunton

2 out of 5
268 N Central Ave, Staunton, VA
Book a stay at this business-friendly hotel in Staunton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (1,004 reviews)
"A great area to look around."

Reviewed on Jul 19, 2025

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Howard Johnson by Wyndham Staunton
Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane, Staunton, VA
Stay at this motel in Staunton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,002 reviews)
"Staff was great!"

Reviewed on Jul 14, 2025

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Motel 6 Staunton, VA
Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

2 out of 5
2060 Rosser Avenue/I-64, I-64 and Exit 94, Waynesboro, VA
Book a stay at this business-friendly motel in Waynesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7/10 Good! (1,005 reviews)
"It was fair"

Reviewed on Jul 7, 2025

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Days Inn by Wyndham Waynesboro
Holiday Inn Express And Suites Staunton by IHG

Holiday Inn Express And Suites Staunton by IHG

2.5 out of 5
47 Rolling Thunder 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 ...
9.4/10 Exceptional! (788 reviews)
"Better pillows will be nice."

Reviewed on Jul 18, 2025

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Holiday Inn Express And Suites Staunton by IHG
Holiday Inn Express And Suites Waynesboro East by IHG

Holiday Inn Express And Suites Waynesboro East by IHG

2.5 out of 5
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. ...
9/10 Wonderful! (379 reviews)
"The room was well maintained, quiet and very clean. All amenities I look for were present (refrigerator, microwave, coffee maker, adequate free parking.) Breakfast was varied and bountiful."

Reviewed on Jul 21, 2025

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Holiday Inn Express And Suites Waynesboro East by IHG
avid hotel Staunton by IHG

avid hotel Staunton by IHG

2.5 out of 5
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 ...
8.8/10 Excellent! (986 reviews)
"Check in lady was great. Check in was fast and efficient . She was very friendly and made us feel welcome with big smiles . Only thing we didn’t like was the halls were very noisy at night . Sounded like a lot of boys playing in the hallways talking very loud at a late hour."

Reviewed on Jul 20, 2025

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avid hotel Staunton by IHG
See all 1,194 properties in Wintergreen
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.