$66 Cheap flights to Windham County

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Top places to visit in Windham County

A river with a bridge, a town, and surrounding hills.
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Brattleboro

Brattleboro
A stone structure with a red and white sign reading 'Stratton' and a bear silhouette.
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Stratton

Stratton
A snow-covered landscape with a bench and trees.
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Londonderry

Londonderry

Cheap flights to Windham County from $66 One Way, $135 Round Trip

$135 return flights and $66 one-way flights to Windham County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 17 - Sun, Feb 21
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 11 hours ago
$135
Roundtrip
found 11 hours ago
Select Cape Air flight, departing Wed, Feb 17 from Boston to Lebanon, returning Sun, Feb 21, priced at $135 found 11 hours ago
Fri, Jan 1 - Thu, Jan 7
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 16 hours ago
$145
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $145 found 16 hours ago
Mon, Nov 16 - Mon, Nov 16
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Cape Air flight, departing Mon, Nov 16 from Boston to Rutland, returning Mon, Nov 16, priced at $154 found 2 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 16 hours ago
$155
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $155 found 16 hours ago
Sun, Nov 15 - Sun, Nov 15
BOS
Boston
LEB
Lebanon
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Cape Air flight, departing Sun, Nov 15 from Boston to Lebanon, returning Sun, Nov 15, priced at $160 found 4 days ago
Thu, Feb 4 - Mon, Feb 8
BWI
Baltimore
LEB
Lebanon
$372 Roundtrip, found 14 hours ago
$372
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Feb 4 from Baltimore to Lebanon, returning Mon, Feb 8, priced at $372 found 14 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCONorth ClarendonNovember 22 to November 26$609
DCANorth ClarendonNovember 22 to November 23$617
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Windham County Accommodation Deals

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
1254 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $60 total per night from Nov 15 to Nov 16
$60 total
Nov 15 - Nov 16
Total with taxes and fees
Stay at this motel in Brattleboro. Enjoy free WiFi, free parking, and room service. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl ...
Opens in a new windowTravelodge by Wyndham Brattleboro VT
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Nov 15 to Nov 16
$105 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
Opens in a new windowColonial Motel
Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

2 out of 5
515 Canal St Brattleboro VT
Fully refundable
$99 nightly
The price is $109 total per night from Dec 13 to Dec 14
$109 total
Dec 13 - Dec 14
Total with taxes and fees
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
Opens in a new windowEcono Lodge Brattleboro South
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The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
420 Magic Mountain Access Road Londonderry VT
$88 nightly
The price is $96 total per night from Nov 16 to Nov 17
$96 total
Nov 16 - Nov 17
Total with taxes and fees
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. ...
8.2/10 Very Good! (715 reviews)
"Loretta was so helpful and friendly."

Reviewed on Nov 12, 2026

Opens in a new windowThe Upper Pass Lodge at Magic Mountain
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.

Our Top Windham County Apartment Hotels

Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out

Dover VT
Book a stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are ...
9.8/10 Exceptional! (205 reviews)
"Great location, beautiful surroundings. Our kids loved the fun games and Nintendo!"

Reviewed on Oct 19, 2026

Get rates
Opens in a new windowSeasons On Mount Snow - Ski-in/Ski-out
Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
$260 nightly
The price is $294 total per night from Nov 15 to Nov 16
$294 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this ski hotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Tamarack Ski Lift ...
Opens in a new windowVantage Point Villas at Stratton Mountain Resort
Mount Snow Condominiums

Mount Snow Condominiums

3.5 out of 5
89 Grand Summit Way West Dover VT
Stay at this condo in West Dover. Enjoy free parking, a 24-hour front desk, and cable TV channels. Popular attractions Mount Snow and Tumbleweed Ski Lift are ...
7.6/10 Good! (80 reviews)
SMELLY
"We were very disappointed,the check in went smooth,but the condo itself was very disappointing.The minute we walked in the building it smelled terrible.Had no clue it was a basement condo or never would of booked it. The linen and couch itself smelled moldy and musty..there was a huge rip in the ..."

Reviewed on Aug 10, 2018

Get rates
Opens in a new windowMount Snow Condominiums
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.

Score Epic Windham County Accommodation Deals

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
$173 nightly
The price is $190 total per night from Nov 16 to Nov 17
$190 total
Nov 16 - Nov 17
Total with taxes and fees
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 ...
Opens in a new windowGrand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Nov 15 to Nov 16
$105 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
Opens in a new windowColonial Motel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $147 total per night from Dec 1 to Dec 2
$147 total
Dec 1 - Dec 2
Total with taxes and fees
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. ...
Opens in a new windowLatchis Hotel
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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
$151 nightly
The price is $166 total per night from Nov 15 to Nov 16
$166 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
Opens in a new windowThe Black Bear Lodge at Stratton Mountain Resort
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.

Family Friendly Hotels in Windham County

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
420 Magic Mountain Access Road Londonderry VT
$88 nightly
The price is $96 total per night from Nov 16 to Nov 17
$96 total
Nov 16 - Nov 17
Total with taxes and fees
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. ...
8.2/10 Very Good! (715 reviews)
"Loretta was so helpful and friendly."

Reviewed on Nov 12, 2026

Opens in a new windowThe Upper Pass Lodge at Magic Mountain
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Nov 15 to Nov 16
$105 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
Opens in a new windowColonial Motel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $130 total per night from Nov 19 to Nov 20
$130 total
Nov 19 - Nov 20
Total with taxes and fees
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 ...
Opens in a new windowHampton Inn Brattleboro
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The Black Bear Lodge at Stratton Mountain Resort
Great for families

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
$151 nightly
The price is $166 total per night from Nov 15 to Nov 16
$166 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
Opens in a new windowThe Black Bear Lodge at Stratton Mountain Resort
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Windham County

Why search for low cost fares on your flights to Windham County when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Windham County

Orbitz offers massive discounts and substantial last-minute savings on your Windham County flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Windham County flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Windham County. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Windham County but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Windham County?
With 12 airlines venturing to Albany Intl. Airport (ALB), you'll be exploring every corner of Windham County in no time at all. Choosing a flight that suits your travel plans is easy as pie. Take a look at the fares from these top carriers and prepare for a smooth landing at Albany Intl. Airport (ALB):

  • American Airlines - 139 flights to Windham County per month
  • Delta - 135 flights to Windham County per month
  • United Airlines - 129 flights to Windham County per month

How much is a flight to Windham County?
Return flights to Windham County this past week ranged from $135 to $617. If you were flying one-way from Boston (BOS), you could have bagged ticket prices from as low as $66.
How to book the cheapest flight to Windham County?
With some of the best flight deals around, you can jet for less with Orbitz. The following pointers will help you find cheap flights to Windham County — and leave you with extra cash in your wallet:

  • Taking off from or arriving at other airports may work out to be cheaper. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below the form fields to see your options.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' option. You'll see the flight deals for the days either side of your chosen departure. Ticket prices often vary depending on the day of the week.
  • You can also hit the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • Reserve your airfare as soon as you've sorted your travel dates. While it does happen now and then, airline tickets rarely fall in price as your date of departure nears.
  • Save even more on your adventure by combining your hotel, flights and car rentals into one convenient package deal. Your budget will thank you for it.
  • Flying during the busy season can mean pricey airfares. Try to vacation outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Windham County?
Snap up a bargain and secure your seats to Windham County in January. If you've missed this month, you're still in luck. February and August often have affordable airfares too. Make sure you don't sleep on a sale — cheap flights come and go in the click of a button!
What day of the week is the cheapest to book a flight to Windham County?
Land a fantastic flight deal by making a booking on a Tuesday, Wednesday or Saturday. These are typically the best days of the week to pick up cheap fares to Windham County.
What is the cheapest day of the week to fly to Windham County?
If you're looking for cheap flights to Windham County, leave earlier in the week. Orbitz data from 2020 shows Monday is the most affordable day to set off, followed by Tuesday. Saturday is the most expensive, so avoid flying on this day and do your bank account a favor.
What is the cheapest month to fly to Windham County?
Get set to jet for less in August. This is generally the best month to take off if you want cheap flights to Windham County, Orbitz data shows. The costliest time to fly is June, so avoid this month if you're watching your pennies.
Which airlines allow free cancellation?
We know that plans change and flexibility matters. That's why you can search for flights that include free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll show you fares more flexible than candy in a car on a hot day!
What do I need for the flight to Windham County?
Whether you're a regular flyer or you're new to the skies, it helps to be prepared when traveling. Here are some key things to take into consideration:

  • Travel documents such as e-tickets and some identification will be required. To avoid any unnecessary delays at check-in, make sure your booking is made with the exact name, birth date and gender as listed on your current ID.
  • A well-stocked carry-on bag is important for any medium-haul journey. With several hours up your sleeve, you'll probably long for something to keep you amused while in transit. We suggest a good book (or trashy magazine), and something to nibble on.
  • Plane cabins can get quite cold. Even if you're traveling during the peak of summer, make sure you take a sweater on board to keep comfortable.

How do I get cheap first-class/business deals to Windham County?
If you think a business or first-class airfare is out of your reach, think again. Here are some top tips to help you find a premium flight to Windham County for less:

  • Be more flexible with your travel dates and wait for sales on business or first-class airfares.
  • Budget airlines offer first or business-class seats at affordable prices. Ditch the full-service carriers and check out these cheaper options.
  • Bid for an upgrade in online auctions or upgrade with loyalty points.

What is the best time to go to Windham County?
There's no good or bad time to head to Windham County, but January, August and December are the most popular months. For most places in the Northern Hemisphere, summer kicks off June 20. If you'd like to get around in a lightweight top than a winter coat, this time of year may be perfect for you. Expect average daytime highs of 75 ºF and nighttime lows around 55 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.