Cheap Flights to Windham County from $90 (2026/2027)

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Mount Snow

West Dover

Flights
West Dover

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.

Sun, Jun 28 - Thu, Jul 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sun, Jun 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 2, priced at $180 found 2 days ago
Sun, Jul 5 - Sun, Jul 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 16 hours ago
$184
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Sun, Jul 5 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jul 12, priced at $184 found 16 hours ago
Thu, Jul 23 - Wed, Jul 29
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Jul 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 29, priced at $186 found 1 day ago
Sun, Jul 5 - Sun, Jul 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 16 hours ago
$190
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Sun, Jul 5 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jul 12, priced at $190 found 16 hours ago
Thu, Jul 23 - Wed, Jul 29
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Jul 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 29, priced at $190 found 1 day ago
Mon, Aug 24 - Mon, Sep 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Aug 24 from Logan Intl. to Lebanon Municipal, returning Mon, Sep 14, priced at $190 found 1 day ago
Sun, Jun 28 - Sat, Jul 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Jun 28 from Logan Intl. to Lebanon Municipal, returning Sat, Jul 4, priced at $194 found 4 days ago
Mon, Aug 24 - Sun, Aug 30
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$384 Roundtrip, found 1 day ago
$384
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Aug 24 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Aug 30, priced at $384 found 1 day ago
OriginDestinationTravel DatesFlights From*
DCAWest LebanonJuly 14 to July 29$394
DCANorth ClarendonAugust 20 to August 26$401
TPANorth ClarendonJuly 10 to July 17$504
ATLNorth ClarendonJune 16 to June 19$505
TPAWest LebanonJune 7 to June 13$514
ATLWest LebanonJune 11 to June 23$517
ORDNorth ClarendonJuly 5 to July 9$524
LAXWest LebanonAugust 25 to September 2$535
FLLNorth ClarendonJuly 17 to July 22$541
FLLWest LebanonJuly 7 to July 7$543
MCOWest LebanonAugust 5 to August 10$565
ORDWest LebanonJune 18 to July 1$599
DENWest LebanonAugust 20 to August 29$605
LAXNorth ClarendonJune 24 to June 29$607
DENNorth ClarendonJuly 25 to August 16$699
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DCAWest LebanonMay 31 to June 4$564
TPANorth ClarendonMay 30 to June 6$649
LAXNorth ClarendonMay 30 to June 5$688
ATLWest LebanonMay 31 to June 2$696
DCANorth ClarendonMay 29 to May 31$706
MCONorth ClarendonMay 30 to June 2$803
TPAWest LebanonMay 29 to June 1$810
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chalet 239
2.0-star property

Chalet 239

Jul 26 - Jul 30

4 night stay

Tampa (TPA) to Springfield (VSF)

Breeze Airways • Non-stop roundtrip • Coach
Price was $649, price is now $539 per person
$539
per person
found 7 hours ago
The Quechee Inn at Marshland Farm
3.0-star property

The Quechee Inn at Marshland Farm

Jul 26 - Jul 30

4 night stay

Tampa (TPA) to Rutland (RUT)

Breeze Airways • Non-stop roundtrip • Coach
Price was $736, price is now $602 per person
$602
per person
found 7 hours ago
Latchis Hotel
2.5-star property

Latchis Hotel

Jul 26 - Jul 30

4 night stay

Tampa (TPA) to Springfield (VSF)

Breeze Airways • Non-stop roundtrip • Coach
Price was $715, price is now $591 per person
$591
per person
found 7 hours ago
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Travelers ❤️ These Windham County 🏨

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! (980 reviews)
"Easy to get to. Basic amenities. Breakfast ok…"

Reviewed on May 22, 2026

Opens in a new windowHampton Inn Brattleboro
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! (884 reviews)
"Great"

Reviewed on May 19, 2026

Opens in a new windowLatchis Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this 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 New England Center for Circus Arts are located nearby.
Opens in a new windowColonial Motel And Spa
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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! (268 reviews)
"Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful"

Reviewed on May 2, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
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 $180 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 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 $180. 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 $180 and $810. 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.
How long is the average flight to Windham County?
The length of your direct flight to Windham County is typically dependent on your starting point. If you'd like an idea of what to expect, here are the average travel times for a handful of leading routes to Windham County:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 2 hours and 1 minute
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Albany Intl. Airport (ALB) - 1 hour and 32 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Albany Intl. Airport (ALB) - 1 hour and 16 minutes

What can I expect on a flight to Windham County?
This mainly depends on where you're departing from and which carrier you fly with. You're likely to find all kinds of flights to Windham County, from first class trips to cheap flights for family vacations. If you're traveling long haul, your airline will typically provide hot meals and entertainment as well as games to amuse the kids.