Windham County Vacations & Trips from $294
Book a Hotel + Flight or Car together to unlock savings
Your Windham County Vacation
Make organizing your next big adventure simple with a Windham County vacation package. Whether it's the food scene, history or something else entirely that lures you here, our packages will help you experience the best of it. Want to know where to go during your trip to Windham County? Plainfield is a top city that shouldn't be missed. From the instant you book your Windham County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top destinations in Windham County
Willimantic
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The General Stanton Inn
Price was $369, price is now $294 per person
$294
per person
Feb 5 - Feb 7
found 24 hours ago
Roundtrip flight included
New York (NYC) to Providence (PVD)
9.4/10 Exceptional! (153 reviews)
The food in the dining room was delicious. Nice atmosphere. We would probably come back again to eat and stay the night.
Reviewed on Nov 9, 2026
Chart House Inn
Downtown Newport
Price was $1,015, price is now $847 per person
$847
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Providence (PVD)
9/10 Wonderful! (155 reviews)
Inn keeper MIA the whole time.
Amenities not available.
Shower leaked in the floor.
Reviewed on Nov 6, 2026
Find the Best Windham County Vacation Packages
Windham County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 23,100 |
Top Sights | Moosup Pond Beach, Nickerson Park and Harrisville Golf Course |
Windham County Hotel Deals
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $120 total per night from Nov 16 to Nov 17
$120 total
Nov 16 - Nov 17
Total with taxes and fees
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $89 total per night from Dec 13 to Dec 14
$89 total
Dec 13 - Dec 14
Total with taxes and fees
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.
Stay near popular Windham County attractions
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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.