Flights To Windham County - Cheap Flights Starting at CA $355

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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.

Mon, Sep 21 - Tue, Sep 29
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $622 Roundtrip, found 1 day ago
CA $622
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 21 from Pearson Intl. to Lebanon Municipal, returning Tue, Sep 29, priced at CA $622 found 1 day ago
Wed, Aug 19 - Wed, Aug 26
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $650 Roundtrip, found 1 day ago
CA $650
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 19 from Pearson Intl. to Lebanon Municipal, returning Wed, Aug 26, priced at CA $650 found 1 day ago
Wed, Aug 19 - Wed, Aug 26
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $664 Roundtrip, found 1 day ago
CA $664
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 19 from Pearson Intl. to Lebanon Municipal, returning Wed, Aug 26, priced at CA $664 found 1 day ago
Mon, Sep 21 - Tue, Sep 29
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $664 Roundtrip, found 1 day ago
CA $664
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 21 from Pearson Intl. to Lebanon Municipal, returning Tue, Sep 29, priced at CA $664 found 1 day ago
Mon, Sep 21 - Tue, Sep 29
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 21 from Pearson Intl. to Lebanon Municipal, returning Tue, Sep 29, priced at CA $672 found 1 day ago
Mon, Sep 21 - Tue, Sep 29
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $702 Roundtrip, found 1 day ago
CA $702
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 21 from Pearson Intl. to Lebanon Municipal, returning Tue, Sep 29, priced at CA $702 found 1 day ago
Wed, Aug 19 - Wed, Aug 26
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $703 Roundtrip, found 1 day ago
CA $703
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 19 from Pearson Intl. to Lebanon Municipal, returning Wed, Aug 26, priced at CA $703 found 1 day ago
Wed, Aug 19 - Wed, Aug 26
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $710 Roundtrip, found 1 day ago
CA $710
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 19 from Pearson Intl. to Lebanon Municipal, returning Wed, Aug 26, priced at CA $710 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Jun 30 - Jul 3

3 night stay

Halifax (YHZ) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $1,274, price is now CA $1,150 per person
CA $1,150
per person
found 3 hours ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Sep 17 - Sep 21

4 night stay

Calgary (YYC) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $2,173, price is now CA $1,842 per person
CA $1,842
per person
just found
Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

Jul 17 - Jul 20

3 night stay

Montreal (YMQ) to Rutland (RUT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,693, price is now CA $1,518 per person
CA $1,518
per person
found 1 day 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! (908 reviews)
"Perfect location. The hotel itself is historic but feels dated because of gaps in maintenance. Lack of restaurant is noted though lots of options just outside the property. Staff at the front desk is very friendly and provided great recommendations."

Reviewed on Jun 24, 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! (998 reviews)
"Fantastic lodging for our business trip!"

Reviewed on Jun 23, 2026

Opens in a new windowHampton Inn Brattleboro
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! (1,000 reviews)
"convenient to the freeway. Light and Airy room. good Internet reception."

Reviewed on Jun 21, 2026

Opens in a new windowThe Putney Inn
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Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library are located nearby.
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on May 25, 2026

Opens in a new windowAmazing 34 foot high shipping container home in Whitingham on Sadawga Lake
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 $622 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 $622. 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 $622 and CA $710. 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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