Flights To Windham County - Cheap Flights Starting at CA $122

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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.

Mon, Oct 5 - Mon, Oct 12
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $244 Roundtrip, found 4 days ago
CA $244
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Oct 5 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 12, priced at CA $244 found 4 days ago
Mon, Oct 12 - Sat, Oct 17
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $245 Roundtrip, found 1 day ago
CA $245
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Oct 12 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 17, priced at CA $245 found 1 day ago
Sun, Oct 4 - Sun, Oct 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $252 Roundtrip, found 3 days ago
CA $252
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sun, Oct 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 11, priced at CA $252 found 3 days ago
Mon, Oct 5 - Mon, Oct 12
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $258 Roundtrip, found 4 days ago
CA $258
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Oct 5 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 12, priced at CA $258 found 4 days ago
Mon, Oct 12 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $260 Roundtrip, found 1 day ago
CA $260
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Oct 12 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at CA $260 found 1 day ago
Sun, Oct 4 - Sun, Oct 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $266 Roundtrip, found 3 days ago
CA $266
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sun, Oct 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 11, priced at CA $266 found 3 days ago
Mon, Oct 5 - Mon, Oct 12
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $273 Roundtrip, found 4 days ago
CA $273
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Oct 5 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 12, priced at CA $273 found 4 days ago
Thu, Oct 15 - Tue, Oct 20
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $274 Roundtrip, found 1 day ago
CA $274
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Oct 15 from Logan Intl. to Lebanon Municipal, returning Tue, Oct 20, priced at CA $274 found 1 day ago

Travelers ❤️ These Windham County 🏨

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 a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
8.6/10 Excellent! (308 reviews)
"Pool and hot tub were closed, no fresh towels or maid service or coffee replenishment. No shuttle service available and no coffee cups provided in the lobby for complimentary coffee. The bar closed at 8:30 even though posted hours were until 10:00"

Reviewed on Sep 7, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
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! (982 reviews)
"What a unique hotel! If you love vintage everything and downtown living, this is your spot. There have been thoughtful updates to the property for functionality and comfort, but many details of the property were kept intact for period charm. Some features are older (plumbing, bath fixtures, door ..."

Reviewed on Sep 13, 2026

Opens in a new windowLatchis Hotel
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. 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 (57 reviews)
"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

Reviewed on Sep 14, 2026

Opens in a new windowColonial Motel
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Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 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.
8.6/10 Excellent! (131 reviews)
"A Complete Health Hazard – Please Read Before Booking My family and I visit Vermont five to six times a year. We love this state, which makes writing this deeply saddening. Our experience at the Hideaway Inn Mt. Snow on September 5, 2026, was a horrifying exception to the wonderful hospitality we ..."

Reviewed on Sep 12, 2026

Opens in a new windowHideaway Inn Mt. Snow
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 $244 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 October. 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 $244. 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 $244 and CA $520. 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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