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, Jan 9 - Mon, Jan 12
BUF
Buffalo Niagara Intl.
RUT
Rutland Southern Vermont Regional
CA $648 Roundtrip, found 4 hours ago
CA $648
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Fri, Jan 9 from Buffalo Niagara Intl. to Rutland Southern Vermont Regional, returning Mon, Jan 12, priced at CA $648 found 4 hours ago
Price found within the past 48 hours. Click for updated prices.
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 1 day ago
Treehouse Home in Ludlow
2.0-star property

Treehouse Home in Ludlow

Dec 25 - Dec 29

4 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $12,718, price is now CA $11,153 per person
CA $11,153
per person
found 1 day ago
Hidden Kingdom in Plymouth
2.0-star property

Hidden Kingdom in Plymouth

Dec 25 - Dec 29

4 night stay

Toronto (YYZ) to Rutland (RUT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $5,727, price is now CA $5,113 per person
CA $5,113
per person
found 1 day 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! (939 reviews)
Overall, a comfortable stay, although the hotel is a bit dated, and doesn't offer many frills. Some areas of the hotel are showing a lot of wear and tear, but nothing that kept us from enjoying our stay. One thing to note, the walls and floors in this hotel don't offer much in terms of noise dampening. ...

Reviewed on Dec 15, 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 $648 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 1 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 January. 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 $648. 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 $648 and CA $648. 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.