Flights To Windham County - Cheap Flights Starting at

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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.

Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $991 Roundtrip, found 3 days ago
CA $991
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $991 found 3 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,081 Roundtrip, found 3 days ago
CA $1,081
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,081 found 3 days ago
Wed, Jun 24 - Wed, Jul 15
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,084 Roundtrip, found 3 days ago
CA $1,084
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 24 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Jul 15, priced at CA $1,084 found 3 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,102 Roundtrip, found 3 days ago
CA $1,102
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,102 found 3 days ago
Mon, Dec 29 - Mon, Jan 5
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,130 Roundtrip, found 19 hours ago
CA $1,130
Roundtrip
found 19 hours ago
Select Delta flight, departing Mon, Dec 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Mon, Jan 5, priced at CA $1,130 found 19 hours ago
Mon, Dec 29 - Mon, Jan 5
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,143 Roundtrip, found 19 hours ago
CA $1,143
Roundtrip
found 19 hours ago
Select Delta flight, departing Mon, Dec 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Mon, Jan 5, priced at CA $1,143 found 19 hours ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,144 Roundtrip, found 3 days ago
CA $1,144
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,144 found 3 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,158 Roundtrip, found 3 days ago
CA $1,158
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,158 found 3 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,170 Roundtrip, found 3 days ago
CA $1,170
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,170 found 3 days ago
Wed, Jun 24 - Wed, Jul 15
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,178 Roundtrip, found 3 days ago
CA $1,178
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 24 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Wed, Jul 15, priced at CA $1,178 found 3 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,197 Roundtrip, found 3 days ago
CA $1,197
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,197 found 3 days ago
Mon, Jan 5 - Mon, Jan 12
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,204 Roundtrip, found 6 days ago
CA $1,204
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 5 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Mon, Jan 12, priced at CA $1,204 found 6 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,207 Roundtrip, found 3 days ago
CA $1,207
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,207 found 3 days ago
Mon, Jan 5 - Mon, Jan 12
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,230 Roundtrip, found 6 days ago
CA $1,230
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Jan 5 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Mon, Jan 12, priced at CA $1,230 found 6 days ago
Wed, Apr 29 - Thu, Jun 4
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,233 Roundtrip, found 3 days ago
CA $1,233
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Thu, Jun 4, priced at CA $1,233 found 3 days ago
OriginDestinationTravel datesFlights from*
DCANorth ClarendonJanuary 1 to January 7CA $529
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort
2.0-star property

North Star Lodge and Resort

Feb 12 - Feb 16

4 night stay

Toronto (YYZ) to Rutland (RUT)

Delta • Non-stop roundtrip • Coach
Price was CA $1,514, price is now CA $1,399 per person
CA $1,399
per person
found 16 hours ago
Mount Snow Grand Summit Resort
3.0-star property

Mount Snow Grand Summit Resort

Feb 12 - Feb 16

4 night stay

Toronto (YYZ) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $3,257, price is now CA $2,768 per person
CA $2,768
per person
found 16 hours ago
Jackson Gore Village
3.0-star property

Jackson Gore Village

Dec 25 - Dec 29

4 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $3,387, price is now CA $3,045 per person
CA $3,045
per person
found 16 hours ago
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Travelers ❤️ These Windham County 🏨

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
Book a stay at this 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! (243 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

Opens in a new windowMount Snow Grand Summit Resort
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! (1,001 reviews)
Room very nice, comfortable clean

Reviewed on Nov 29, 2025

Opens in a new windowThe Covered Bridge Inn
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
Book a stay at this ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stratton Mountain Resort and Villager Ski Lift are located nearby.
7.6/10 Good! (937 reviews)
Complimentary breakfast was nice. Room was clean.

Reviewed on Dec 8, 2025

Opens in a new windowThe Black Bear Lodge at Stratton Mountain Resort
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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! (925 reviews)
Convenient, clean. Staff was very friendly and helpful. Close to Highway. Keys weren’t working when we returned from a long day out. TV was also not working, but luckily we were in the room for only a short time before heading out for dinner.

Reviewed on Dec 8, 2025

Opens in a new windowHampton Inn Brattleboro
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 $529 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 April. 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 $529. 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 $529 and CA $1,233. 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.