Flights To Windham County - Cheap Flights Starting at

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

Stratton

Flights
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.

Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $705 Roundtrip, found 5 days ago
CA $705
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $705 found 5 days ago
Wed, Mar 11 - Fri, Apr 3
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $712 Roundtrip, found 3 days ago
CA $712
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Mar 11 from Pearson Intl. to Lebanon Municipal, returning Fri, Apr 3, priced at CA $712 found 3 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $719 Roundtrip, found 5 days ago
CA $719
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $719 found 5 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $722 Roundtrip, found 5 days ago
CA $722
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $722 found 5 days ago
Sun, Apr 5 - Sun, Apr 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $724 Roundtrip, found 13 hours ago
CA $724
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Apr 5 from Pearson Intl. to Lebanon Municipal, returning Sun, Apr 12, priced at CA $724 found 13 hours ago
Wed, Mar 11 - Fri, Apr 3
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $725 Roundtrip, found 3 days ago
CA $725
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Mar 11 from Pearson Intl. to Lebanon Municipal, returning Fri, Apr 3, priced at CA $725 found 3 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $735 Roundtrip, found 5 days ago
CA $735
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $735 found 5 days ago
Wed, Mar 11 - Fri, Apr 3
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $743 Roundtrip, found 3 days ago
CA $743
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Mar 11 from Pearson Intl. to Lebanon Municipal, returning Fri, Apr 3, priced at CA $743 found 3 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $752 Roundtrip, found 5 days ago
CA $752
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $752 found 5 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $761 Roundtrip, found 5 days ago
CA $761
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $761 found 5 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $775 Roundtrip, found 5 days ago
CA $775
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $775 found 5 days ago
Wed, Mar 11 - Fri, Apr 3
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $783 Roundtrip, found 3 days ago
CA $783
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Mar 11 from Pearson Intl. to Lebanon Municipal, returning Fri, Apr 3, priced at CA $783 found 3 days ago
Mon, Mar 9 - Wed, Apr 1
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $785 Roundtrip, found 5 days ago
CA $785
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Mar 9 from Pearson Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at CA $785 found 5 days ago
Sun, Apr 5 - Sun, Apr 12
YYZ
Pearson Intl.
LEB
Lebanon Municipal
CA $787 Roundtrip, found 13 hours ago
CA $787
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Apr 5 from Pearson Intl. to Lebanon Municipal, returning Sun, Apr 12, priced at CA $787 found 13 hours ago
Thu, Aug 20 - Mon, Aug 31
YYC
Calgary Intl.
LEB
Lebanon Municipal
CA $1,070 Roundtrip, found 1 day ago
CA $1,070
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Aug 20 from Calgary Intl. to Lebanon Municipal, returning Mon, Aug 31, priced at CA $1,070 found 1 day ago
OriginDestinationTravel datesFlights from*
TPAWest LebanonApril 2 to April 9CA $779
DCAWest LebanonApril 24 to May 10CA $887
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Quechee Inn at Marshland Farm
3.0-star property

The Quechee Inn at Marshland Farm

Apr 17 - Apr 20

3 night stay

Toronto (YYZ) to Rutland (RUT)

Delta • Non-stop roundtrip • Coach
Price was CA $975, price is now CA $898 per person
CA $898
per person
found 1 day ago
Grand Summit Resort, A Vail Resorts Property
3.0-star property

Grand Summit Resort, A Vail Resorts Property

Mar 16 - Mar 20

4 night stay

Toronto (YTO) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $2,066, price is now CA $1,842 per person
CA $1,842
per person
found 14 hours ago
The Mountain Inn at Killington
2.5-star property

The Mountain Inn at Killington

Mar 16 - Mar 20

4 night stay

Toronto (YTO) to Rutland (RUT)

Delta • Non-stop roundtrip • Coach
Price was CA $1,562, price is now CA $1,427 per person
CA $1,427
per person
found 14 hours ago
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Travelers ❤️ These Windham County 🏨

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
8.8/10 Excellent! (67 reviews)
Refrigerator in rooms, but no elevators

Reviewed on Mar 1, 2026

Opens in a new windowHideaway Inn Mt. Snow
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! (978 reviews)
yes ski slopes were easily accessible

Reviewed on Mar 7, 2026

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

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and daily housekeeping. 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! (1,003 reviews)
My room was clean and spacious. Bed was very comfortable. Mini fridge and microwave a big plus! I normally stay at a different hotel when I come up to visit my family but I decided to try this hotel. I wasn't sure how it would be but I was pleasantly surprised! Clean, quiet and the gentleman who ...

Reviewed on Feb 27, 2026

Opens in a new windowThe Covered Bridge Inn
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Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 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 helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
8.6/10 Excellent! (780 reviews)
I liked it a lot for the one night stop

Reviewed on Mar 5, 2026

Opens in a new windowComfort Inn & Suites Brattleboro I-91
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 $705 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 March. 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 $705. 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 $705 and CA $1,070. 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.