$40 Cheap flights to Windham County

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Top places to visit in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
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Brattleboro

Brattleboro

Cheap flights to Windham County from $40 One Way, $137 Round Trip

$137 return flights and $40 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, Apr 30 - Tue, Apr 30
BOS
Boston
RUT
Rutland
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Apr 30 from Boston to Rutland, returning Tue, Apr 30, priced at $137 found 1 day ago
Mon, Apr 29 - Tue, Apr 30
BOS
Boston
RUT
Rutland
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Apr 29 from Boston to Rutland, returning Tue, Apr 30, priced at $139 found 1 day ago
Tue, Apr 30 - Tue, Apr 30
BOS
Boston
RUT
Rutland
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Cape Air flight, departing Tue, Apr 30 from Boston to Rutland, returning Tue, Apr 30, priced at $140 found 1 day ago
Sat, Apr 27 - Sun, Apr 28
BOS
Boston
RUT
Rutland
$143 Roundtrip, found 9 hours ago
$143
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Sat, Apr 27 from Boston to Rutland, returning Sun, Apr 28, priced at $143 found 9 hours ago
Sat, Jul 13 - Sat, Jul 13
BOS
Boston
LEB
Lebanon
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Jul 13 from Boston to Lebanon, returning Sat, Jul 13, priced at $153 found 6 days ago
Thu, Jun 20 - Wed, Jun 26
HPN
White Plains
LEB
Lebanon
$220 Roundtrip, found 6 hours ago
$220
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Thu, Jun 20 from White Plains to Lebanon, returning Wed, Jun 26, priced at $220 found 6 hours ago
Sun, May 26 - Tue, Jun 4
DCA
Washington
LEB
Lebanon
$321 Roundtrip, found 7 hours ago
$321
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Sun, May 26 from Washington to Lebanon, returning Tue, Jun 4, priced at $321 found 7 hours ago
Thu, Aug 1 - Thu, Aug 8
DCA
Washington
RUT
Rutland
$326 Roundtrip, found 5 days ago
$326
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 1 from Washington to Rutland, returning Thu, Aug 8, priced at $326 found 5 days ago

Deals For This Weekend's Flights

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
The price is $90 per night from Apr 28 to Apr 29
$90
per night
Apr 28 - Apr 29
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 (625 reviews)
Good value for a 1 night stay, but not luxurious
"Garrett was wonderful at the front desk . He was able to accommodate a room on the first floor which was important for my family. He was respectful and professional and went the extra mile to provide a late check out of 2 hours so I could get additional rest after a long trip. The room was clean ..."

Reviewed on Dec 15, 2023

Travelodge by Wyndham Brattleboro VT
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $123 per night from May 1 to May 2
$123
per night
May 1 - May 2
Stay at this 3-star 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 ...
6.8/10 (1,000 reviews)
"Very comfortable"

Reviewed on Apr 21, 2024

Colonial Motel And Spa
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $113 per night from Apr 28 to Apr 29
$113
per night
Apr 28 - Apr 29
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
5.6/10 (482 reviews)
"Clean quiet and affordable place with a friendly staff. Small critique: put a small shelf in the shower for shampoo/soap etc."

Reviewed on Oct 16, 2023

Econo Lodge Brattleboro
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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
The price is $60 per night from May 7 to May 8
$60
per night
May 7 - May 8
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (550 reviews)
"Quiet"

Reviewed on Apr 15, 2024

The 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
Stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and onsite parking. Popular attractions Mount Snow and Seasons Ski Lift are located ...
9.6/10 Exceptional! (137 reviews)
"Carl was super nice, proactive, and a great communicator for this trip. The place was convenient, clean, in great repair, with lots of amenities and super easy to ski out. Little touches like a box of firewood, tinder, and matches and clear instructions on everything make things so pleasant. Would ..."

Reviewed on Apr 18, 2024

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Seasons 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
The price is $245 per night from Apr 28 to Apr 29
$245
per night
Apr 28 - Apr 29
Stay at this 3-star 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! (59 reviews)
"Very comfortable condo near the Stratton Mountain lifts. Very comfortable beds, lots of extra bedding. We would definitely stay here again."

Reviewed on Apr 8, 2024

Vantage 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 3.5-star condo in West Dover. Enjoy free parking, a 24-hour front desk, and a TV. Popular attractions Mount Snow and Tumbleweed Ski Lift are located ...
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
Mount 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

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $72 per night from Apr 28 to Apr 29
$72
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,002 reviews)
"Beds were squeaky but rooms are big"

Reviewed on Apr 19, 2024

The Covered Bridge Inn
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $123 per night from May 1 to May 2
$123
per night
May 1 - May 2
Stay at this 3-star 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 ...
6.8/10 (1,000 reviews)
"Very comfortable"

Reviewed on Apr 21, 2024

Colonial Motel And Spa
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
Stay at this 3-star spa resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.4/10 Good! (827 reviews)
"It is an excellent ski hotel with friendly service and great beds."

Reviewed on Apr 8, 2024

Get rates
The Black Bear Lodge at Stratton Mountain Resort
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $114 per night from Apr 29 to Apr 30
$114
per night
Apr 29 - Apr 30
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and internet. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (893 reviews)
"Good stay"

Reviewed on Apr 13, 2024

Hampton Inn Brattleboro
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
Great for families

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
420 Magic Mountain Access Road, Londonderry, VT
The price is $60 per night from May 7 to May 8
$60
per night
May 7 - May 8
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (550 reviews)

Families like: Outdoor pools, skiing nearby, bicycle rentals nearby

Travelers say...
"Quiet"

Reviewed on Apr 15, 2024

The Upper Pass Lodge at Magic Mountain
Colonial Motel And Spa
Great for families

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $123 per night from May 1 to May 2
$123
per night
May 1 - May 2
Stay at this 3-star 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 ...
6.8/10 (1,000 reviews)

Families like: Indoor pools, skiing nearby

Travelers say...
"Very comfortable"

Reviewed on Apr 21, 2024

Colonial Motel And Spa
Hampton Inn Brattleboro
Great for families

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is $114 per night from Apr 29 to Apr 30
$114
per night
Apr 29 - Apr 30
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and internet. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (893 reviews)

Families like: Indoor pools, skiing nearby, extra beds/cribs, free breakfast for the whole family

Travelers say...
"Good stay"

Reviewed on Apr 13, 2024

Hampton 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
Stay at this 3-star spa resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.4/10 Good! (827 reviews)

Families like: Game room, babysitting, skiing nearby, bicycle rentals nearby

Travelers say...
"It is an excellent ski hotel with friendly service and great beds."

Reviewed on Apr 8, 2024

Get rates
The 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 or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Windham County

When you plan to buy tickets for flights to Windham County, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Windham County flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Windham County Flights

Orbitz offers deeply discounted flights to Windham County, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Windham County? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Windham County flights.

Frequently asked questions

Which airlines fly to Windham County?
With 16 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 $137 to $326. If you were flying one-way from Boston (BOS), you could have bagged ticket prices from as low as $40.
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.

City Destinations in Windham County

More Popular Airlines

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.