Flights To Windham County - Cheap Flights Starting at CA $375

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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, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $877 Roundtrip, found 1 day ago
CA $877
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $877 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $880 Roundtrip, found 1 day ago
CA $880
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $880 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $893 Roundtrip, found 1 day ago
CA $893
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $893 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $899 Roundtrip, found 1 day ago
CA $899
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $899 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $921 Roundtrip, found 1 day ago
CA $921
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $921 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $945 Roundtrip, found 1 day ago
CA $945
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $945 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $947 Roundtrip, found 1 day ago
CA $947
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $947 found 1 day ago
Fri, Jul 3 - Sun, Jul 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $954 Roundtrip, found 1 day ago
CA $954
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 3 from Pearson Intl. to Lebanon Municipal, returning Sun, Jul 12, priced at CA $954 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
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 4 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5-star property

Killington Mountain Lodge, Tapestry Collection by Hilton

Jun 15 - Jun 21

6 night stay

Toronto (YTO) to Rutland (RUT)

Delta • Non-stop roundtrip • Coach
Price was CA $1,762, price is now CA $1,472 per person
CA $1,472
per person
found 16 hours ago
Jackson Gore Village, A Vail Resorts Property
3.0-star property

Jackson Gore Village, A Vail Resorts Property

Jun 15 - Jun 21

6 night stay

Toronto (YTO) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $1,846, price is now CA $1,561 per person
CA $1,561
per person
found 16 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! (272 reviews)
"Excellent stay, looking forward to visiting again!"

Reviewed on Jun 8, 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 $877 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 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 CA $877. 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 $877 and CA $954. 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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