$66 Cheap flights to Windham County

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Top places to visit in Windham County

A calm lake reflecting a forest with autumn foliage.
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Brattleboro

Brattleboro
A forest with autumn foliage reflecting in a calm lake.
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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, $130 Round Trip

$130 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.

Sat, Jan 2 - Sat, Jan 2
BOS
Boston
LEB
Lebanon
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Cape Air flight, departing Sat, Jan 2 from Boston to Lebanon, returning Sat, Jan 2, priced at $130 found 5 days ago
Wed, Jan 6 - Wed, Jan 13
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 7 hours ago
$135
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Wed, Jan 6 from Boston to Lebanon, returning Wed, Jan 13, priced at $135 found 7 hours ago
Sat, Jan 2 - Sat, Jan 2
BOS
Boston
LEB
Lebanon
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Cape Air flight, departing Sat, Jan 2 from Boston to Lebanon, returning Sat, Jan 2, priced at $140 found 5 days ago
Wed, Jan 6 - Wed, Jan 13
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 7 hours ago
$145
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Wed, Jan 6 from Boston to Lebanon, returning Wed, Jan 13, priced at $145 found 7 hours ago
Fri, Jan 15 - Fri, Jan 15
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Jan 15 from Boston to Rutland, returning Fri, Jan 15, priced at $154 found 1 day ago
Sun, Dec 20 - Sat, Dec 26
HPN
White Plains
LEB
Lebanon
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Cape Air flight, departing Sun, Dec 20 from White Plains to Lebanon, returning Sat, Dec 26, priced at $180 found 5 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDWest LebanonNovember 1 to November 2$654
MCOWest LebanonNovember 1 to November 5$903
*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
$62 nightly
The price is $68 total per night from Nov 2 to Nov 3
$68 total
Nov 2 - Nov 3
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 1 to Nov 2
$105 total
Nov 1 - Nov 2
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 Nov 29 to Nov 30
$109 total
Nov 29 - Nov 30
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
$94 nightly
The price is $103 total per night from Nov 29 to Nov 30
$103 total
Nov 29 - Nov 30
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. ...
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
$252 nightly
The price is $285 total per night from Nov 1 to Nov 2
$285 total
Nov 1 - Nov 2
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 ...
8.4/10 Very Good! (71 reviews)
"Beautiful, secluded little area up in the mountain. It was so nice that there was firewood and a wood burning fireplace inside the property."

Reviewed on Jun 26, 2026

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
Fully refundable
$172 nightly
The price is $189 total per night from Nov 2 to Nov 3
$189 total
Nov 2 - Nov 3
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 ...
8.6/10 Excellent! (326 reviews)
"We went for a wedding and couldn’t have been happier with our stay."

Reviewed on Oct 25, 2026

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 1 to Nov 2
$105 total
Nov 1 - Nov 2
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
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from Nov 2 to Nov 3
$116 total
Nov 2 - Nov 3
Total with taxes and fees
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 ...
Opens in a new windowHideaway Inn Mt. Snow
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Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $159 total per night from Nov 3 to Nov 4
$159 total
Nov 3 - Nov 4
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
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
$94 nightly
The price is $103 total per night from Nov 29 to Nov 30
$103 total
Nov 29 - Nov 30
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. ...
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 1 to Nov 2
$105 total
Nov 1 - Nov 2
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
$110 nightly
The price is $121 total per night from Nov 15 to Nov 16
$121 total
Nov 15 - Nov 16
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
$149 nightly
The price is $164 total per night from Nov 1 to Nov 2
$164 total
Nov 1 - Nov 2
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

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Windham County or any other low fare domestic or international air travel.

Innovative Orbitz Tools for the Trip Planner on the Move

Now it is even faster to find exclusive deals and book cheap Windham County flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Windham County's most popular attractions, best restaurants, and entertainment venues or check on your flights to Windham County and make changes to your itinerary while waiting in line for your latte.

Stay on Budget, Earn Miles with Bargain Windham County Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Windham County. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Windham County flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Windham County to your mobile phone or email.

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 $130 to $903. 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.