Flights To Windham County - Cheap Flights Starting at

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Autumn colors along Connecticut River, Brattleboro, Vermont

Brattleboro

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Brattleboro
Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak

Stratton

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Stratton

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.

Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $731 Roundtrip, found 4 days ago
CA $731
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $731 found 4 days ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $776 Roundtrip, found 4 days ago
CA $776
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $776 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $794 Roundtrip, found 4 days ago
CA $794
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $794 found 4 days ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $845 Roundtrip, found 4 days ago
CA $845
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $845 found 4 days ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $865 Roundtrip, found 4 days ago
CA $865
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $865 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $922 Roundtrip, found 4 days ago
CA $922
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $922 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $932 Roundtrip, found 4 days ago
CA $932
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $932 found 4 days ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $935 Roundtrip, found 4 days ago
CA $935
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $935 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $940 Roundtrip, found 4 days ago
CA $940
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $940 found 4 days ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $954 Roundtrip, found 4 days ago
CA $954
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $954 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,002 Roundtrip, found 4 days ago
CA $1,002
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $1,002 found 4 days ago
Sun, Jun 14 - Wed, Jul 1
YUL
Pierre Elliott Trudeau Intl.
RUT
Rutland Southern Vermont Regional
CA $1,003 Roundtrip, found 16 hours ago
CA $1,003
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sun, Jun 14 from Pierre Elliott Trudeau Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 1, priced at CA $1,003 found 16 hours ago
Sat, May 30 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,005 Roundtrip, found 4 days ago
CA $1,005
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 30 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $1,005 found 4 days ago
Wed, Jun 3 - Wed, Aug 19
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,010 Roundtrip, found 4 days ago
CA $1,010
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jun 3 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Aug 19, priced at CA $1,010 found 4 days ago
Sun, Jun 14 - Wed, Jul 1
YUL
Pierre Elliott Trudeau Intl.
RUT
Rutland Southern Vermont Regional
CA $1,026 Roundtrip, found 16 hours ago
CA $1,026
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sun, Jun 14 from Pierre Elliott Trudeau Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 1, priced at CA $1,026 found 16 hours ago
Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn
2.5-star property

The Covered Bridge Inn

May 3 - May 6

3 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,400, price is now CA $1,247 per person
CA $1,247
per person
found 1 day ago
The Quechee Inn at Marshland Farm
3.0-star property

The Quechee Inn at Marshland Farm

May 3 - May 6

3 night stay

Toronto (YYZ) to Rutland (RUT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,393, price is now CA $1,265 per person
CA $1,265
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

May 3 - May 6

3 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,352, price is now CA $1,252 per person
CA $1,252
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Windham County 🏨

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! (967 reviews)
We were well taken care of the whole time. Just a great all around experience

Reviewed on Apr 28, 2026

Opens in a new windowHampton Inn Brattleboro
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. 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.
6.8/10 (1,001 reviews)
Awesome and clean and quiet love the staff

Reviewed on Apr 14, 2026

Opens in a new windowColonial Motel And Spa
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! (872 reviews)
I enjoyed my stay at the Latchis very much. It was my first time there since 2018 and hope to make a return trip again very soon!

Reviewed on Apr 27, 2026

Opens in a new windowLatchis Hotel
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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.
8.4/10 Very Good! (1,000 reviews)
Very friendly staff (owner). Older roadside motel type property but very convenient for Landmark College and very clean. Definitely would stay again when visiting our kiddo at school.

Reviewed on Apr 26, 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 $731 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 June. 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 $731. 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 $731 and CA $1,026. 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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