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.

Fri, Jun. 12 - Sun, Jun. 14
DTW
Detroit Metropolitan Wayne County
RUT
Rutland Southern Vermont Regional
CA $637 Roundtrip, found 1 day ago
CA $637
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Jun. 12 from Detroit Metropolitan Wayne County to Rutland Southern Vermont Regional, returning Sun, Jun. 14, priced at CA $637 found 1 day ago
Fri, Jun. 12 - Sun, Jun. 14
DTW
Detroit Metropolitan Wayne County
RUT
Rutland Southern Vermont Regional
CA $678 Roundtrip, found 1 day ago
CA $678
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Jun. 12 from Detroit Metropolitan Wayne County to Rutland Southern Vermont Regional, returning Sun, Jun. 14, priced at CA $678 found 1 day ago
Tue, Aug. 26 - Fri, Sep. 5
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
CA $868 Roundtrip, found 3 days ago
CA $868
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug. 26 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Fri, Sep. 5, priced at CA $868 found 3 days ago
Tue, Aug. 26 - Fri, Sep. 5
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
CA $881 Roundtrip, found 3 days ago
CA $881
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug. 26 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Fri, Sep. 5, priced at CA $881 found 3 days ago
Tue, Aug. 26 - Fri, Sep. 5
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
CA $959 Roundtrip, found 3 days ago
CA $959
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug. 26 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Fri, Sep. 5, priced at CA $959 found 3 days ago
Tue, Aug. 26 - Fri, Sep. 5
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
CA $973 Roundtrip, found 3 days ago
CA $973
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug. 26 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Fri, Sep. 5, priced at CA $973 found 3 days ago
Sun, Sep. 7 - Thu, Sep. 11
YEG
Edmonton Intl.
LEB
Lebanon Municipal
CA $2,207 Roundtrip, found 1 day ago
CA $2,207
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, Sep. 7 from Edmonton Intl. to Lebanon Municipal, returning Thu, Sep. 11, priced at CA $2,207 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
The Vermont Inn
3.0-star property

The Vermont Inn

Oct 13 - Oct 20

7 night stay

St. John's (YYT) to Rutland (RUT)

United • Coach

Rutland (RUT) to St. John's (YYT)

Air Canada • Coach
Price was CA $2,269, price is now CA $1,911 per person
CA $1,911
per person
found 14 hours ago
Solitude Village at Okemo
4.0-star property

Solitude Village at Okemo

Oct 13 - Oct 20

7 night stay

St. John's (YYT) to Springfield (VSF)

United • Coach

Springfield (VSF) to St. John's (YYT)

Air Canada • Coach
Price was CA $2,368, price is now CA $2,033 per person
CA $2,033
per person
found 14 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5-star property

Killington Mountain Lodge, Tapestry Collection by Hilton

Oct 13 - Oct 20

7 night stay

St. John's (YYT) to Rutland (RUT)

United • Coach

Rutland (RUT) to St. John's (YYT)

Air Canada • Coach
Price was CA $2,440, price is now CA $2,111 per person
CA $2,111
per person
found 14 hours ago
Don't see what you're looking for?
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Travelers ❤️ These Windham County 🏨

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Stay at this 3-star 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 United States Navy Seabee Bridge are located nearby.
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug. 22, 2025

Colonial Motel And Spa
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.
8/10 Very Good! (870 reviews)
"very friendly , clean and quiet, i would for sure stay if i come this way again. room is nice, beds comfy ,bathroom nice."

Reviewed on Aug. 20, 2025

Hampton Inn Brattleboro
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! (1,003 reviews)
"My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term ..."

Reviewed on Aug. 22, 2025

The Putney Inn
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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.
8.4/10 Very Good! (774 reviews)
"I loved everything about this place. I will be back!"

Reviewed on Aug. 14, 2025

Latchis Hotel
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 $637 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 7 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 $637. 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 $637 and CA $2,207. 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.