Windham County Vacations & Trips from $1,017
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Your Windham County Vacation
Answer the call of adventure with a tailor-made vacation package to Windham County. Wherever it is you're going and whatever you plan to do, prepare to discover a destination with plenty to offer. Kick off your trip to Windham County with a couple of nights in Wilmington visiting popular attractions like Mount Snow and Mount Snow Golf Course. Londonderry is another city that draws crowds from near and far. Magic Mountain Ski Resort and Jamaica State Park are two of the leading places to see in this destination. From the moment you book your Windham County vacation to when you get back home, Expedia has your back every step of the way.
Top destinations in Windham County
Brattleboro
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort
Price was $1,746, price is now $1,366 per person
$1,366
per person
Dec 19 - Dec 25
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
8.6/10 Excellent! (1,003 reviews)
We were very pleased with everything. Our room had a view of construction renovation instead of the mountain view, but we will be back.
Reviewed on Sep 29, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Save 100% on your flight
Price was $2,997, price is now $2,386 per person
$2,386
per person
Dec 26 - Dec 30
found 12 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (48 reviews)
We booked a non-smoking room. Showed up and the place ABSOLUTELY reaked of smoke. The smell was caked into everything including bedding. It was like they were smoking 10 packs plus a day and didn’t leave. Lamps and cabinets were broken as well. Cleaners also showed up at 6am blasting music, which was well before the 11am check out of the property. owners of the property did communicate well and that was much appreciated. However after this stay we are still feeling sub par out this place.
Reviewed on Aug 4, 2025
Windham County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Albany Intl. Airport (ALB) |
Top Sights | Lowell Lake State Park, Molly Stark State Park and Lake Raponda |
Windham County Hotel Deals
Econo Lodge Brattleboro
515 Canal St, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
Total with taxes and fees
5.4/10 (568 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."
Reviewed on Sep 2, 2025
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $139 total per night from Oct 5 to Oct 6
$139 total
Oct 5 - Oct 6
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
"Clean, comfortable room. Modest continental breakfast."
Reviewed on Sep 26, 2025
Latchis Hotel
50 Main Street, Brattleboro, VT
$133 nightly
The price is $147 total per night from Nov 3 to Nov 4
$147 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (797 reviews)
"Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful."
Reviewed on Sep 28, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
