$77 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.

Brattleboro

A forest with autumn foliage reflecting in a calm lake.

Stratton

A snow-covered landscape with a bench and trees.

Londonderry

Cheap flights to Windham County from $77 One Way, $150 Round Trip

$150 return flights and $77 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, Nov 7 - Sat, Nov 7

BOS

Boston

LEB

Lebanon

$150

Roundtrip

found 2 days ago

Tue, Dec 15 - Sat, Dec 19

BOS

Boston

LEB

Lebanon

$155

Roundtrip

found 1 day ago

Tue, Dec 15 - Sat, Dec 19

BOS

Boston

LEB

Lebanon

$165

Roundtrip

found 1 day ago

Sat, Sep 19 - Sat, Sep 19

BOS

Boston

LEB

Lebanon

$172

Roundtrip

found 4 days ago

Sat, Aug 15 - Mon, Aug 17

BOS

Boston

LEB

Lebanon

$175

Roundtrip

found 19 hours ago

Thu, Nov 12 - Mon, Nov 16

BOS

Boston

RUT

Rutland

$180

Roundtrip

found 20 hours ago

Fri, Dec 11 - Sun, Dec 13

MCO

Orlando

RUT

Rutland

$518

Roundtrip

found 17 hours ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
ORD	West Lebanon	August 7 to August 9	$674
ORD	North Clarendon	August 7 to August 9	$705
DCA	West Lebanon	August 7 to August 9	$709
LAX	North Clarendon	August 9 to August 11	$901
ATL	North Clarendon	August 9 to August 10	$931

*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Windham County Accommodation Deals

Travelodge by Wyndham Brattleboro VT

1254 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$74 nightly

$81 total

Aug 4 - Aug 5

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 ...

6/10 (789 reviews)

"The staff were very helpful!"

Reviewed on Jul 29, 2026

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$77 nightly

$84 total

Aug 4 - Aug 5

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 ...

6.8/10 (32 reviews)

"This is a very tired motel. The sign says grand opening, but apparently their grand opening is sometime in the future! Tattered carpets, old drapery, no landscaping to speak of, the lounge area was filled with boxes. The check-in area needed a massive update. Breakfast seemed to have been an afterthought. ..."

Reviewed on Aug 3, 2026

Econo Lodge Brattleboro South

515 Canal St Brattleboro VT

Fully refundable

$89 nightly

$98 total

Aug 9 - Aug 10

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 ...

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The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road Londonderry VT

$107 nightly

$118 total

Sep 2 - Sep 3

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! (702 reviews)

"Great hotel, good location"

Reviewed on Jul 23, 2026

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

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! (194 reviews)

"The unit was perfect for our family get away. We had everything we needed for cooking, and kitchen was well stocked with non parishbles items.Owner communicated well, and even allowed us to check in early, and late check out as it was not being rented before and after us.We will definitely go back.Nice ..."

Reviewed on Jul 13, 2026

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Vantage Point Villas at Stratton Mountain Resort

5 Village Lodge Road Stratton VT

$241 nightly

$272 total

Aug 11 - Aug 12

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

Mount Snow Condominiums

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! (81 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

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

Latchis Hotel

50 Main Street Brattleboro VT

Fully refundableReserve now, pay when you stay

$115 nightly

$126 total

Aug 9 - Aug 10

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. ...

8.6/10 Excellent! (944 reviews)

"We loved the property! The facility is very well renovated, and the staff was very nice! It was full of history, and very interesting for us traveling as a couple. The vinyl record player and the collections were very cool!!! I would recommend to anyone who would like to explore the city have a have ..."

Reviewed on Aug 3, 2026

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Fully refundableReserve now, pay when you stay

$121 nightly

$133 total

Aug 11 - Aug 12

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 ...

8.2/10 Very Good! (1,004 reviews)

"Nice pool and jacuzzi! Co venison to restaurants and shops"

Reviewed on Aug 2, 2026

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$77 nightly

$84 total

Aug 4 - Aug 5

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 ...

6.8/10 (32 reviews)

"This is a very tired motel. The sign says grand opening, but apparently their grand opening is sometime in the future! Tattered carpets, old drapery, no landscaping to speak of, the lounge area was filled with boxes. The check-in area needed a massive update. Breakfast seemed to have been an afterthought. ..."

Reviewed on Aug 3, 2026

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Grand Summit Resort, A Vail Resorts Property

89 Grand Summit Way West Dover VT

Fully refundable

$163 nightly

$179 total

Sep 1 - Sep 2

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! (300 reviews)

"Host in restaurant let us stand at the host stand while he finished up his conversation with friends or regulars at bar until he realized to seat us. Took over 45 minutes to get a hamburger and pork slider sliders. Served to us at 9:00 pm sat at 8:10pm. Needed to hurry because they played the “Closing ..."

Reviewed on Aug 3, 2026

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

420 Magic Mountain Access Road Londonderry VT

$107 nightly

$118 total

Sep 2 - Sep 3

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! (702 reviews)

"Great hotel, good location"

Reviewed on Jul 23, 2026

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$77 nightly

$84 total

Aug 4 - Aug 5

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 ...

6.8/10 (32 reviews)

"This is a very tired motel. The sign says grand opening, but apparently their grand opening is sometime in the future! Tattered carpets, old drapery, no landscaping to speak of, the lounge area was filled with boxes. The check-in area needed a massive update. Breakfast seemed to have been an afterthought. ..."

Reviewed on Aug 3, 2026

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Fully refundableReserve now, pay when you stay

$121 nightly

$133 total

Aug 11 - Aug 12

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 ...

8.2/10 Very Good! (1,004 reviews)

"Nice pool and jacuzzi! Co venison to restaurants and shops"

Reviewed on Aug 2, 2026

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The Black Bear Lodge at Stratton Mountain Resort

5 Village Lodge Road Stratton VT

$142 nightly

$156 total

Aug 10 - Aug 11

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 ...

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

Compact

Ford Focus

4 people

Midsize

Toyota Corolla

5 people

SUV

Jeep Compass

5 people

Windham County

Orbitz uses cutting edge mobile technology to help get you the best deals on Windham County flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Windham County Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Windham County, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Windham County can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Windham County. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Windham County to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Windham County?

With 15 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 $150 to $931. If you were flying one-way from Boston (BOS), you could have bagged ticket prices from as low as $77.

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.