Cheap Flights to Windham County from $79 (2026/2027)

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Brattleboro

Flights
Brattleboro

How Much Does it Cost To Fly To Windham County?

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

Sat, Jul 11 - Fri, Jul 17
BOS
Logan Intl.
LEB
Lebanon Municipal
$162 Roundtrip, found 5 days ago
$162
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Logan Intl. to Lebanon Municipal, returning Fri, Jul 17, priced at $162 found 5 days ago
Mon, Jul 13 - Sun, Jul 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Jul 13 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 19, priced at $168 found 3 days ago
Sat, Jul 11 - Mon, Jul 13
BOS
Logan Intl.
LEB
Lebanon Municipal
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Logan Intl. to Lebanon Municipal, returning Mon, Jul 13, priced at $172 found 1 day ago
Thu, Jul 23 - Mon, Jul 27
BOS
Logan Intl.
LEB
Lebanon Municipal
$172 Roundtrip, found 4 hours ago
$172
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Logan Intl. to Lebanon Municipal, returning Mon, Jul 27, priced at $172 found 4 hours ago
Wed, Jul 22 - Sun, Jul 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$173 Roundtrip, found 19 hours ago
$173
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, Jul 22 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 26, priced at $173 found 19 hours ago
Mon, Jul 13 - Sun, Jul 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 3 days ago
$175
Roundtrip
found 3 days ago
Select Cape Air flight, departing Mon, Jul 13 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 19, priced at $175 found 3 days ago
Fri, Sep 25 - Mon, Sep 28
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 2 days ago
$175
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 25 from Logan Intl. to Lebanon Municipal, returning Mon, Sep 28, priced at $175 found 2 days ago
Fri, Sep 11 - Tue, Sep 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Sep 11 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 15, priced at $180 found 1 day ago
Fri, Jul 31 - Fri, Jul 31
HPN
Westchester County
LEB
Lebanon Municipal
$220 Roundtrip, found 3 hours ago
$220
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Fri, Jul 31 from Westchester County to Lebanon Municipal, returning Fri, Jul 31, priced at $220 found 3 hours ago
OriginDestinationTravel DatesFlights From*
DCAWest LebanonAugust 24 to August 29$377
DCANorth ClarendonSeptember 10 to September 13$444
TPAWest LebanonJuly 21 to July 23$478
TPANorth ClarendonSeptember 17 to September 20$488
MCOWest LebanonJuly 21 to July 28$488
SJUNorth ClarendonSeptember 3 to September 7$500
MCONorth ClarendonOctober 9 to October 13$509
DENNorth ClarendonAugust 4 to August 11$519
ATLWest LebanonSeptember 17 to September 20$525
ATLNorth ClarendonJuly 27 to August 3$546
ORDNorth ClarendonJuly 25 to July 30$562
CLTNorth ClarendonAugust 20 to August 23$640
LAXWest LebanonAugust 5 to August 12$654
DENWest LebanonJuly 22 to July 26$808
LAXNorth ClarendonJuly 27 to July 30$901
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDNorth ClarendonJuly 10 to July 12$594
DCAWest LebanonJuly 10 to July 10$654
DCANorth ClarendonJuly 10 to July 13$766
MCOWest LebanonJuly 12 to July 15$784
DENNorth ClarendonJuly 11 to July 27$784
DENWest LebanonJuly 10 to July 19$859
MCONorth ClarendonJuly 10 to July 12$899
FLLNorth ClarendonJuly 10 to July 15$1,030
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Aug 18 - Aug 22

4 night stay

Chicago (CHI) to Springfield (VSF)

Southwest Airlines • Roundtrip • Coach
Price was $804, price is now $672 per person
$672
per person
found 1 day ago
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Sep 26 - Oct 2

6 night stay

Chicago (ORD) to Rutland (RUT)

United • Roundtrip • Coach
Price was $1,002, price is now $790 per person
$790
per person
found 1 day ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Aug 18 - Aug 22

4 night stay

Chicago (CHI) to Springfield (VSF)

Southwest Airlines • Roundtrip • Coach
Price was $953, price is now $767 per person
$767
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Windham County 🏨

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
8.6/10 Excellent! (288 reviews)
"ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration"

Reviewed on Jul 5, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
8.6/10 Excellent! (922 reviews)
"I love this place. It's really special. Some people to preserve what was special and exciting and authentic about a historic space and these are my people. They have the amenities you need (great bed and linens, refridgerator, microwave, good towels). They have the amenities you don't need but love! ..."

Reviewed on Jul 5, 2026

Opens in a new windowLatchis Hotel
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
5.4/10 (13 reviews)
"The bed was hard to sleep on, the outdoor pool was filled with dirt, the indoor pool/spa/massage area is dilapidated, and the continental breakfast offered the bare minimum. When using the shower, switching from tub to shower was a task in itself while the water pressure was weak"

Reviewed on Jul 6, 2026

Opens in a new windowColonial Motel
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
8.2/10 Very Good! (1,003 reviews)
"Loved the breakfast!"

Reviewed on Jul 5, 2026

Opens in a new windowHampton Inn Brattleboro
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.

Frequently asked questions

How much is the cheapest flight to Windham County?
Some thrifty travelers booked a roundtrip flight to Windham County for as little as $162 in the last seven days. If you spot a bargain, act fast. Cheap deals don't hang around for long! This price was available on Travelocity for flights to Windham County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Windham County?
You can choose from 16 airlines when you're ready to lock in your flight to Windham County. Let Cape Air fly you there. This favorite air carrier offers 182 services per month to Bellows Falls, Windham County's primary city.
What is the cheapest month to fly to Windham County?
For the greatest chance at landing a terrific flight deal, time your break sometime in July. Based on Travelocity's direct flight demand from January to December last year, it's the cheapest time to journey to Windham County.
How can I check my flight status to Windham County?
Check out our helpful portal, Trips. You'll find just about everything related to your flight to Windham County here, including important information about the status of your flight and more. Trips is found at the top right of the Travelocity homepage. Simply sign up, log in and get the answers you need. Alternatively, you can access your itinerary while you're on the go and get real-time travel updates through the Travelocity app. You'll find all your itineraries in one place, making it a snap to share details with any members of your family flying with you.
How do I find the best deals on flights to Windham County?
Be flexible with your dates and there's a strong chance you'll find an amazing deal. After you've searched for flights on Travelocity, hit the "Flexible dates" box at the top of the page to compare prices with nearby days. Also try to book ahead of schedule and avoid the busy tourist season. In the last seven days, the best price for a return flight to Windham County was $162. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Windham County with Travelocity?
Look for cheap flights to Windham County with Travelocity and begin packing for your next vacation. With 24/7 customer service throughout every step of the process and our Price Match Guarantee, we take the stress out of booking cheap family flights, hotels, activities and more. Snag a great deal now and prepare for an epic adventure.
What are the most popular flight routes to Windham County?
As a renowned vacation destination, you'll find excellent connections to Windham County. Check out this sample of popular routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 1,122 flights a month.
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Albany Intl. Airport (ALB) - 706 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Albany Intl. Airport (ALB) - 689 flights a month.

How much is a flight to Windham County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Windham County were between $162 and $1,030. Whenever you're ready to go, Travelocity will help you find a fare that won't blow your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Windham County?
The length of your direct flight to Windham County is typically dependent on your starting point. If you'd like an idea of what to expect, here are the average travel times for a handful of leading routes to Windham County:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 2 hours and 1 minute
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Albany Intl. Airport (ALB) - 1 hour and 32 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Albany Intl. Airport (ALB) - 1 hour and 16 minutes

What can I expect on a flight to Windham County?
This mainly depends on where you're departing from and which carrier you fly with. You're likely to find all kinds of flights to Windham County, from first class trips to cheap flights for family vacations. If you're traveling long haul, your airline will typically provide hot meals and entertainment as well as games to amuse the kids.