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Wintergreen

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Wintergreen Flights as Low as $386

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

American Airlines
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$386 Roundtrip, just found
$386
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $386 just found
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$397 Roundtrip, found 22 hours ago
$397
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 $397 found 22 hours ago
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$398 Roundtrip, found 4 hours ago
$398
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $398 found 4 hours ago
United
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$401 Roundtrip, just found
$401
Roundtrip
just found
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $401 just found
American Airlines
Tue, Sep 23 - Wed, Sep 24
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$404 Roundtrip, found 3 days ago
$404
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Wed, Sep 24, priced at $404 found 3 days ago
United
Tue, Sep 23 - Wed, Sep 24
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Wed, Sep 24, priced at $406 found 1 day ago
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$408 Roundtrip, found 4 hours ago
$408
Roundtrip
found 4 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 4 hours ago
American Airlines
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$409 Roundtrip, just found
$409
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $409 just found
United
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$412 Roundtrip, found 22 hours ago
$412
Roundtrip
found 22 hours ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $412 found 22 hours ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $415 found 3 days ago
American Airlines
Fri, Sep 26 - Mon, Sep 29
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$417 Roundtrip, found 1 day ago
$417
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 26 from Logan Intl. to Shenandoah Valley Regional, returning Mon, Sep 29, priced at $417 found 1 day ago
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$420 Roundtrip, found 4 hours ago
$420
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $420 found 4 hours ago
Contour Airlines
Thu, Jul 10 - Mon, Jul 21
PBG
Plattsburgh Intl.
SHD
Shenandoah Valley Regional
$495 Roundtrip, found 4 days ago
$495
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Thu, Jul 10 from Plattsburgh Intl. to Shenandoah Valley Regional, returning Mon, Jul 21, priced at $495 found 4 days ago
American Airlines
Sat, Jul 5 - Tue, Jul 15
ALB
Albany Intl.
SHD
Shenandoah Valley Regional
$588 Roundtrip, found 6 days ago
$588
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 5 from Albany Intl. to Shenandoah Valley Regional, returning Tue, Jul 15, priced at $588 found 6 days ago
American Airlines
Mon, Jul 14 - Fri, Jul 18
YUL
Pierre Elliott Trudeau Intl.
SHD
Shenandoah Valley Regional
$683 Roundtrip, found 21 hours ago
$683
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Mon, Jul 14 from Pierre Elliott Trudeau Intl. to Shenandoah Valley Regional, returning Fri, Jul 18, priced at $683 found 21 hours ago
American Airlines
Wed, Jul 30 - Tue, Aug 5
HNL
Daniel K. Inouye Intl.
SHD
Shenandoah Valley Regional
$921 Roundtrip, found 23 hours ago
$921
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Wed, Jul 30 from Daniel K. Inouye Intl. to Shenandoah Valley Regional, returning Tue, Aug 5, priced at $921 found 23 hours 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 $386, 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 $386 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! (1,184 reviews)
"like it"

Reviewed on Jun 27, 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! (1,009 reviews)
"We had an excellent stay"

Reviewed on Jun 26, 2025

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Hotel 24 South
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! (1,004 reviews)
"Check-in was fast and easy."

Reviewed on Jun 17, 2025

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Days Inn by Wyndham Waynesboro
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! (1,010 reviews)
Fine place for a night
"My wife and I were taking a weekend trip to Charlottesville and were arriving late the first night. As a result, we only needed something cheap before moving to better accommodations for the next two nights. This place was great. We got a great rate of $67. Property is clean and well maintained. ..."

Reviewed on Jun 28, 2025

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Motel 6 Staunton, VA
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! (356 reviews)
"Breakfast options could have been better. Include better quality fruits and variety."

Reviewed on Jun 24, 2025

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Holiday Inn Express And Suites Waynesboro East by IHG
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! (1,002 reviews)
"Pros: The room itself is very clean and colorful. The A/C was icy cold. It was quiet. Dowtown is walkable and 5 blocks awaywith really good restuarants with outdoor closed-pedestrian street seating. Convenient to the quaint dowtown area. Cons: The exterior of the hotel is aged and gives the impression ..."

Reviewed on Jun 23, 2025

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Howard Johnson by Wyndham Staunton
Comfort Inn
Comfort Inn
2.5 out of 5
15 Windi Grove Drive, Waynesboro, VA
Book a stay at this business-friendly hotel in Waynesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (914 reviews)
"Great service. Good breakfast. Nice place to stay"

Reviewed on Jun 23, 2025

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Comfort Inn
The Blackburn Inn and Conference Center
The Blackburn Inn and Conference Center
3.5 out of 5
301 Greenville Avenue, Staunton, VA
Stay at this 3.5-star hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (992 reviews)
"Such a special property. They did a wonderful renovation with a great balance of historical and modern conveniences. Loves our stay!"

Reviewed on Jun 29, 2025

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The Blackburn Inn and Conference Center
See all 1,198 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.