Cheap Flights to Windham County from $66 (2026/2027)

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West Dover

Flights
West Dover

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.

Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $135 just found
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, just found
$145
Roundtrip
just found
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $145 just found
Fri, Jan 1 - Fri, Jan 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jan 1, priced at $154 found 4 days ago
Tue, Oct 27 - Sat, Oct 31
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 6 hours ago
$155
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Tue, Oct 27 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 31, priced at $155 found 6 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $158 found 1 day ago
Tue, Oct 27 - Sat, Oct 31
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 6 hours ago
$165
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Tue, Oct 27 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 31, priced at $165 found 6 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $168 found 1 day ago
Sat, Dec 26 - Sat, Jan 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select Cape Air flight, departing Sat, Dec 26 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jan 2, priced at $170 found 6 days ago
Fri, Jan 15 - Mon, Jan 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$327 Roundtrip, found 4 days ago
$327
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 15 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Jan 18, priced at $327 found 4 days ago
OriginDestinationTravel DatesFlights From*
DCAWest LebanonJanuary 15 to January 18$327
FLLWest LebanonDecember 9 to December 15$412
MCONorth ClarendonOctober 28 to October 31$412
DCANorth ClarendonDecember 29 to January 2$427
DENNorth ClarendonOctober 24 to October 30$546
MCOWest LebanonNovember 23 to November 28$571
TPANorth ClarendonDecember 12 to December 19$595
TPAWest LebanonDecember 26 to January 3$620
ATLNorth ClarendonDecember 29 to December 31$624
FLLNorth ClarendonOctober 29 to November 5$648
LAXNorth ClarendonOctober 30 to November 2$652
ORDWest LebanonNovember 21 to November 30$679
CLTNorth ClarendonNovember 9 to November 11$904
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLTNorth ClarendonOctober 11 to October 18$771
MCONorth ClarendonOctober 11 to October 13$800
MCOWest LebanonOctober 9 to October 11$808
FLLWest LebanonOctober 9 to October 11$835
LAXNorth ClarendonOctober 10 to October 13$880
DCAWest LebanonOctober 9 to October 12$901
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

Dec 16 - Dec 20

4 night stay

Houston (HOU) to Rutland (RUT)

Southwest Airlines • Non-stop • Coach

Rutland (RUT) to Houston (HOU)

American Airlines • Non-stop • Coach
Price was $744, price is now $560 per person
$560
per person
found 1 day ago
Mountain Green Resort
4.0-star property

Mountain Green Resort

Oct 9 - Oct 12

3 night stay

San Juan (SJU) to Rutland (RUT)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,271, price is now $3,243 per person
$3,243
per person
found 1 day ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Dec 16 - Dec 20

4 night stay

Houston (HOU) to Springfield (VSF)

Southwest Airlines • Non-stop • Coach

Springfield (VSF) to Houston (HOU)

American Airlines • Non-stop • Coach
Price was $1,019, price is now $781 per person
$781
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Houston to Windham County
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Travelers ❤️ These Windham County 🏨

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.
6.4/10 (79 reviews)
"This place is tired. Not many options in the area. Not my first time here. New ownership, but it doesn't look or feel any different. Plumbing back ups in sink and tub. Moved the trashcan and there was trash and dirt behind it. Stain on comforter. You know, tired."

Reviewed on Oct 5, 2026

Opens in a new windowColonial Motel
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 a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
8.6/10 Excellent! (313 reviews)
"1"

Reviewed on Oct 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.
Opens in a new windowLatchis Hotel
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Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
8.6/10 Excellent! (138 reviews)
"Really good place"

Reviewed on Oct 4, 2026

Opens in a new windowHideaway Inn Mt. Snow
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 $135 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 January. 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 $135. 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 $135 and $904. 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.