Flights To Windham County - Cheap Flights Starting at CA $56

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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.

Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $262 Roundtrip, found 20 hours ago
CA $262
Roundtrip
found 20 hours ago
Select Cape Air flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $262 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $267 Roundtrip, found 20 hours ago
CA $267
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $267 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $276 Roundtrip, found 20 hours ago
CA $276
Roundtrip
found 20 hours ago
Select Cape Air flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $276 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $277 Roundtrip, found 20 hours ago
CA $277
Roundtrip
found 20 hours ago
Select Cape Air flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $277 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $281 Roundtrip, found 20 hours ago
CA $281
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $281 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $282 Roundtrip, found 20 hours ago
CA $282
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $282 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $290 Roundtrip, found 20 hours ago
CA $290
Roundtrip
found 20 hours ago
Select Cape Air flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $290 found 20 hours ago
Tue, Oct 21 - Thu, Nov 13
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $291 Roundtrip, found 20 hours ago
CA $291
Roundtrip
found 20 hours ago
Select Cape Air flight, departing Tue, Oct 21 from Logan Intl. to Lebanon Municipal, returning Thu, Nov 13, priced at CA $291 found 20 hours ago
Mon, Apr 20 - Thu, Apr 30
YWG
Winnipeg James Armstrong Richardson Intl.
LEB
Lebanon Municipal
CA $1,139 Roundtrip, found 17 hours ago
CA $1,139
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Apr 20 from Winnipeg James Armstrong Richardson Intl. to Lebanon Municipal, returning Thu, Apr 30, priced at CA $1,139 found 17 hours ago

Travelers ❤️ These Windham County 🏨

Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
8.6/10 Excellent! (527 reviews)
Autumn visit in Vermont 2025
"The internet was a bit intermittent on the first day I arrived, but it became more stable on my second day and there after. I didn't use the AC, had the window open the whole time, which was lovely; smelling the Vermont fresh air. The pillows were a bit full and hard but the bed seemed ok. It was ..."

Reviewed on Oct 9, 2025

Opens in a new windowMountaineer Inn
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
8.6/10 Excellent! (230 reviews)
Fall weekend
"Great property, junior suite was perfect. All that we could ask for. Will be back next fall if not sooner."

Reviewed on Oct 11, 2025

Opens in a new windowMount Snow Grand Summit Resort
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located nearby.
5.4/10 (578 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."

Reviewed on Sep 2, 2025

Opens in a new windowEcono Lodge Brattleboro
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The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. 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.
7.6/10 Good! (1,011 reviews)
"There was a band-aid in the bed but I really didn’t care. Seemed clean otherwise. And I could have always used the other bed."

Reviewed on Oct 10, 2025

Opens in a new windowThe Covered Bridge Inn
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 CA $262 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 October. 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 CA $262. 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 CA $262 and CA $1,139. 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.

Destinations in Windham County

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.