$77 Cheap flights to Windham County
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Top places to visit in Windham County
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.
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DCA | West Lebanon | August 9 to August 10 | $522 |
| ORD | West Lebanon | August 9 to August 22 | $558 |
| ORD | North Clarendon | August 7 to August 9 | $705 |
| TPA | West Lebanon | August 7 to August 9 | $782 |
| LAX | North Clarendon | August 9 to August 11 | $901 |
| ATL | North Clarendon | August 9 to August 10 | $931 |
Find The Perfect Hotel For After Your Flight
Score Epic Windham County Accommodation Deals
Travelodge by Wyndham Brattleboro VT
"The staff were very helpful!"
Reviewed on Jul 29, 2026
Colonial Motel
Econo Lodge Brattleboro South
"The room was clean and the bed was comfortable. The bathroom was clean, nice condition, had clean towels, soap and shampoo. Air conditioning worked. The property owner had a large black pipe run along the inside of the room for the second floor above my room. It looked hideous. The outside was not ..."
Reviewed on Jul 27, 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
"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
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
Hampton Inn Brattleboro
"We called down to the desk the night we checked in to get help with TV. Said someone would be up in 10 minutes but that person never showed up. In the morning we called again and the person came shortly but we had to leave the room. Why?"
Reviewed on Aug 1, 2026
Colonial Motel
Comfort Inn & Suites Brattleboro I-91
"Property not well kept on the outside. Location terrible. Are did not have much to offer"
Reviewed on Jul 31, 2026
Family Friendly Hotels in Windham County
The Upper Pass Lodge at Magic Mountain
"Great hotel, good location"
Reviewed on Jul 23, 2026
Colonial Motel
Hampton Inn Brattleboro
"We called down to the desk the night we checked in to get help with TV. Said someone would be up in 10 minutes but that person never showed up. In the morning we called again and the person came shortly but we had to leave the room. Why?"
Reviewed on Aug 1, 2026
The Black Bear Lodge at Stratton Mountain Resort
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Windham County
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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.