Flights To Windham County - Cheap Flights Starting at CA $516

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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.

Thu, Aug 13 - Mon, Aug 17
YVR
Vancouver Intl.
LEB
Lebanon Municipal
CA $956 Roundtrip, found 1 day ago
CA $956
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver Intl. to Lebanon Municipal, returning Mon, Aug 17, priced at CA $956 found 1 day ago
Sun, Jul 19 - Thu, Jul 23
YVR
Vancouver Intl.
RUT
Rutland Southern Vermont Regional
CA $1,048 Roundtrip, found 1 day ago
CA $1,048
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jul 19 from Vancouver Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at CA $1,048 found 1 day ago
Thu, Jun 25 - Wed, Jul 1
YVR
Vancouver Intl.
RUT
Rutland Southern Vermont Regional
CA $1,125 Roundtrip, found 16 hours ago
CA $1,125
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Jun 25 from Vancouver Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 1, priced at CA $1,125 found 16 hours ago
Thu, Aug 13 - Mon, Aug 17
YVR
Vancouver Intl.
LEB
Lebanon Municipal
CA $1,191 Roundtrip, found 1 day ago
CA $1,191
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver Intl. to Lebanon Municipal, returning Mon, Aug 17, priced at CA $1,191 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
YVR
Vancouver Intl.
LEB
Lebanon Municipal
CA $1,199 Roundtrip, found 1 day ago
CA $1,199
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver Intl. to Lebanon Municipal, returning Mon, Aug 17, priced at CA $1,199 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
YVR
Vancouver Intl.
LEB
Lebanon Municipal
CA $1,204 Roundtrip, found 1 day ago
CA $1,204
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver Intl. to Lebanon Municipal, returning Mon, Aug 17, priced at CA $1,204 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
YVR
Vancouver Intl.
LEB
Lebanon Municipal
CA $1,212 Roundtrip, found 1 day ago
CA $1,212
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver Intl. to Lebanon Municipal, returning Mon, Aug 17, priced at CA $1,212 found 1 day ago
Sun, Jul 19 - Thu, Jul 23
YVR
Vancouver Intl.
RUT
Rutland Southern Vermont Regional
CA $1,315 Roundtrip, found 1 day ago
CA $1,315
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jul 19 from Vancouver Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at CA $1,315 found 1 day ago
OriginDestinationTravel datesFlights from*
FLLWest LebanonSeptember 3 to September 6CA $654
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Aug 4 - Aug 8

4 night stay

Toronto (YYZ) to Springfield (VSF)

Air Canada • Roundtrip • Coach
Price was CA $1,295, price is now CA $1,066 per person
CA $1,066
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Aug 24 - Aug 28

4 night stay

Calgary (YYC) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,517, price is now CA $1,286 per person
CA $1,286
per person
found 1 day ago
Chalet 239
2.0-star property

Chalet 239

Aug 24 - Aug 28

4 night stay

Calgary (YYC) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,228, price is now CA $1,121 per person
CA $1,121
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! (905 reviews)
"Love the historical aspects of this place."

Reviewed on Jun 17, 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! (995 reviews)
"Room clean if just a bit worn. Sheets had better days. Helpful staff."

Reviewed on Jun 15, 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! (276 reviews)
"All aspects of the property were excellent and well maintained. The food, service, gym, pool all top notch."

Reviewed on Jun 17, 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! (1,001 reviews)
"No complaints would go back"

Reviewed on Jun 19, 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 $654 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 August. 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 $654. 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 $654 and CA $1,315. 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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