Flights To Windham County - Cheap Flights Starting at CA $338

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Autumn colors along Connecticut River, Brattleboro, Vermont

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.

Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $656 Roundtrip, found 16 hours ago
CA $656
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $656 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $670 Roundtrip, found 16 hours ago
CA $670
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $670 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $671 Roundtrip, found 16 hours ago
CA $671
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $671 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $677 Roundtrip, found 16 hours ago
CA $677
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $677 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $684 Roundtrip, found 16 hours ago
CA $684
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $684 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $691 Roundtrip, found 16 hours ago
CA $691
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $691 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $705 Roundtrip, found 16 hours ago
CA $705
Roundtrip
found 16 hours ago
Select Delta flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $705 found 16 hours ago
Fri, Sep 4 - Mon, Sep 7
BUF
Buffalo Niagara Intl.
LEB
Lebanon Municipal
CA $713 Roundtrip, found 16 hours ago
CA $713
Roundtrip
found 16 hours ago
Select Delta flight, departing Fri, Sep 4 from Buffalo Niagara Intl. to Lebanon Municipal, returning Mon, Sep 7, priced at CA $713 found 16 hours ago
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Aug 19 - Aug 22

3 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,157, price is now CA $1,034 per person
CA $1,034
per person
found 10 hours ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Aug 19 - Aug 22

3 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,611, price is now CA $1,390 per person
CA $1,390
per person
found 10 hours ago
Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

Aug 19 - Aug 22

3 night stay

Toronto (YYZ) to Rutland (RUT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,231, price is now CA $1,129 per person
CA $1,129
per person
found 10 hours ago
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Travelers ❤️ These Windham County 🏨

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! (901 reviews)
"This truly a gem! One of two remaining historic hotels in Detroit, everything about this hotel was something special. The room was spacious and creatively decorated with a large selection of LP's in the hallway. This also included a record player. The queen size beds were extremely comfortable. The ..."

Reviewed on Jun 12, 2026

Opens in a new windowLatchis Hotel
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! (992 reviews)
"Amazing stay! Loved this place!"

Reviewed on Jun 13, 2026

Opens in a new windowHampton Inn Brattleboro
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! (273 reviews)
"Beautiful property! No breakfast there or coffee cups at the coffee station (had to bring your cups from your room). Had some kids running up and down the halls til about 11:00 pm, but that’s on the parents not the hotel."

Reviewed on Jun 15, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
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The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
8.6/10 Excellent! (1,002 reviews)
"Excellent basic comfortable hotel room. There is a fridge and microwave, the hotel was quiet, and the staff were courteous. Everything was very clean. Location is convenient. Highly recommended!"

Reviewed on Jun 14, 2026

Opens in a new windowThe Putney 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 $656 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 15 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 September. 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 $656. 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 $656 and CA $713. 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.

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