$76 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 $76 One Way, $145 Round Trip

$145 return flights and $76 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.

Tue, Dec 29 - Fri, Jan 1

BOS

Boston

LEB

Lebanon

$145

Roundtrip

found 1 day ago

Sat, Nov 21 - Sun, Nov 29

BOS

Boston

LEB

Lebanon

$155

Roundtrip

found 2 days ago

Thu, Nov 5 - Sun, Nov 8

BOS

Boston

LEB

Lebanon

$158

Roundtrip

found 1 day ago

Fri, Feb 5 - Mon, Feb 8

BOS

Boston

RUT

Rutland

$160

Roundtrip

found 1 day ago

Sun, Nov 15 - Sat, Nov 21

BOS

Boston

LEB

Lebanon

$165

Roundtrip

found 2 days ago

Thu, Nov 5 - Sun, Nov 8

BOS

Boston

LEB

Lebanon

$168

Roundtrip

found 1 day ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
CLT	West Lebanon	September 18 to September 21	$722
MCO	West Lebanon	September 18 to September 20	$768
LAX	North Clarendon	September 19 to October 3	$803

*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

$67 nightly

$73 total

Sep 16 - Sep 17

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 ...

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$84 nightly

$93 total

Sep 20 - Sep 21

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 (57 reviews)

"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

Reviewed on Sep 14, 2026

Econo Lodge Brattleboro South

515 Canal St Brattleboro VT

Fully refundable

$99 nightly

$109 total

Oct 13 - Oct 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 ...

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The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road Londonderry VT

$95 nightly

$104 total

Sep 15 - Sep 16

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! (706 reviews)

"The check in process was very frustrating. I booked through Expedia and wasn’t able to access my reservations through their online booking portal. A lodge TV at gas rooms dates in the 70s should probably have staff to check in if they can’t keep up with the technology"

Reviewed on Sep 8, 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! (201 reviews)

"Location is greatSize of unit was greatOwner did communicate greatBut kitchen counter and sink were dirty.The windows are so old most don’t open.If it was warm it would have been awful.Bathrooms are new so they are great."

Reviewed on Sep 6, 2026

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Vantage Point Villas at Stratton Mountain Resort

5 Village Lodge Road Stratton VT

$236 nightly

$266 total

Sep 20 - Sep 21

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! (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

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

89 Grand Summit Way West Dover VT

Fully refundable

$172 nightly

$189 total

Sep 15 - Sep 16

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! (308 reviews)

"Pool and hot tub were closed, no fresh towels or maid service or coffee replenishment. No shuttle service available and no coffee cups provided in the lobby for complimentary coffee. The bar closed at 8:30 even though posted hours were until 10:00"

Reviewed on Sep 7, 2026

Latchis Hotel

50 Main Street Brattleboro VT

Fully refundableReserve now, pay when you stay

$135 nightly

$148 total

Sep 15 - Sep 16

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! (982 reviews)

"What a unique hotel! If you love vintage everything and downtown living, this is your spot. There have been thoughtful updates to the property for functionality and comfort, but many details of the property were kept intact for period charm. Some features are older (plumbing, bath fixtures, door ..."

Reviewed on Sep 13, 2026

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$84 nightly

$93 total

Sep 20 - Sep 21

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 (57 reviews)

"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

Reviewed on Sep 14, 2026

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Hideaway Inn Mt. Snow

270 Handle Rd West Dover VT

Fully refundableReserve now, pay when you stay

$125 nightly

$137 total

Sep 15 - Sep 16

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 ...

8.6/10 Excellent! (131 reviews)

"A Complete Health Hazard – Please Read Before Booking My family and I visit Vermont five to six times a year. We love this state, which makes writing this deeply saddening. Our experience at the Hideaway Inn Mt. Snow on September 5, 2026, was a horrifying exception to the wonderful hospitality we ..."

Reviewed on Sep 12, 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

$95 nightly

$104 total

Sep 15 - Sep 16

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! (706 reviews)

"The check in process was very frustrating. I booked through Expedia and wasn’t able to access my reservations through their online booking portal. A lodge TV at gas rooms dates in the 70s should probably have staff to check in if they can’t keep up with the technology"

Reviewed on Sep 8, 2026

Colonial Motel

889 Putney Rd Brattleboro VT

Fully refundableReserve now, pay when you stay

$84 nightly

$93 total

Sep 20 - Sep 21

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 (57 reviews)

"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

Reviewed on Sep 14, 2026

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Fully refundableReserve now, pay when you stay

$130 nightly

$143 total

Sep 21 - Sep 22

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! (1,001 reviews)

"Great place for overnight stay"

Reviewed on Sep 12, 2026

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The Black Bear Lodge at Stratton Mountain Resort

5 Village Lodge Road Stratton VT

$146 nightly

$160 total

Oct 14 - Oct 15

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

If you are looking for affordable flights to Windham County, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Windham County now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Windham County flights. With Orbitz, booking flights to Windham County is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Windham County flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Windham County flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Windham County flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

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 $145 to $803. If you were flying one-way from Boston (BOS), you could have bagged ticket prices from as low as $76.

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.