$76 Cheap flights to Windham County
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Top places to visit in Windham County
Cheap flights to Windham County from $76 One Way, $155 Round Trip
$155 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.
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | West Lebanon | August 21 to August 28 | $628 |
| DCA | West Lebanon | August 21 to August 24 | $660 |
Find The Perfect Hotel For After Your Flight
Score Epic Windham County Accommodation Deals
Travelodge by Wyndham Brattleboro VT
Colonial Motel
"The room which we stayed at the motel had a strong oder possibly the smell of "skunk." We checked the pool area and it was completely empty and the hot tub was green. I understand that the motel is under new management and I hope they are able to fix the place up."
Reviewed on Aug 13, 2026
Econo Lodge Brattleboro South
"Place was a dump. Walked in the room and walked out. Not fit to stay in. Currently in a dispute for a refund"
Reviewed on Aug 12, 2026
The Upper Pass Lodge at Magic Mountain
"Great hotel, good location"
Reviewed on Jul 23, 2026
Our Top Windham County Apartment Hotels
Seasons On Mount Snow - Ski-in/Ski-out
"Great location in the off season"
Reviewed on Aug 10, 2026
Vantage Point Villas at Stratton Mountain Resort
"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
"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
Score Epic Windham County Accommodation Deals
Latchis Hotel
"BAD, Did not stay after seeing the room. No refund."
Reviewed on Aug 12, 2026
Hampton Inn Brattleboro
"After this experience, I was shown just how poorly Hilton values its guests. When my family faced a medical emergency, management refused to make any reasonable accommodations or offer any meaningful assistance. It felt as though the only priority was taking our money, rather than showing compassion ..."
Reviewed on Aug 14, 2026
Colonial Motel
"The room which we stayed at the motel had a strong oder possibly the smell of "skunk." We checked the pool area and it was completely empty and the hot tub was green. I understand that the motel is under new management and I hope they are able to fix the place up."
Reviewed on Aug 13, 2026
Comfort Inn & Suites Brattleboro I-91
Family Friendly Hotels in Windham County
The Upper Pass Lodge at Magic Mountain
"Great hotel, good location"
Reviewed on Jul 23, 2026
Colonial Motel
"The room which we stayed at the motel had a strong oder possibly the smell of "skunk." We checked the pool area and it was completely empty and the hot tub was green. I understand that the motel is under new management and I hope they are able to fix the place up."
Reviewed on Aug 13, 2026
Hampton Inn Brattleboro
"After this experience, I was shown just how poorly Hilton values its guests. When my family faced a medical emergency, management refused to make any reasonable accommodations or offer any meaningful assistance. It felt as though the only priority was taking our money, rather than showing compassion ..."
Reviewed on Aug 14, 2026
The Black Bear Lodge at Stratton Mountain Resort
Families like: Game room, babysitting, skiing nearby, bicycle rentals nearby
"Rooms and beds were very comfortable. Shower was great - everything was great except the rugs inside the rooms are old and felt damp always. Maybe it was more about the humidity but they just felt gross. I really enjoyed the hot tub, sauna and being able to go up to the village which had so many ..."
Reviewed on Aug 10, 2026
Need a Car For After Your Flight?
Economy
Compact
Midsize
SUV
Windham County
Get the absolute lowest prices on flights to Windham County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.
Book Your Flight To Windham County Using Your Mobile Device
New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Windham County flights.
Avoid Check-In Hassles When Traveling On Flights to Windham County
Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Windham County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.
Keeping Everyone Up To Date
When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.
Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Windham County flight using Orbitz.
Frequently asked questions
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.