Windham County Vacations & Trips from $704
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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
Plainfield
Willimantic
Woodstock
Putnam
Thompson
Brooklyn
Ashford
Dayville
Pomfret
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Fox Point Landing Residences
Fox Point
$704
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Washington (WAS) to Providence (PVD)
10/10 Exceptional! (4 reviews)
The apartment was wonderful. It was clean and beautifully decorated. Parking was a breeze. The location was fantastic. Close to the park, the university district, and restaurants.
Try Marvin Pizza is amazing.
We have stayed in a number of places all around the world and your apartment was among the best.
Reviewed on Aug 8, 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
Best Western Mystic Hotel
48 Whitehall Ave Mystic CT
Fully refundableReserve now, pay when you stay
$137 nightly
$158 total
Aug 30 - Aug 31
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
$88 nightly
$101 total
Sep 13 - Sep 14
Total with taxes and fees
7.8/10 Good! (2,878 reviews)
"Likes is that location was convenient."
Reviewed on Aug 13, 2026
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$103 nightly
$119 total
Sep 1 - Sep 2
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
Thompson International Speedway
8.8/10 (15 reviews)
Catch an event at Thompson International Speedway during your trip to Thompson. Attend a sporting event while you're in the area, or simply enjoy its restaurants.
Brooklyn Recreation Park
8.0/10 (1 review)
Explore the great outdoors at Brooklyn Recreation Park, a lovely green space in Brooklyn. Take some time to visit the casinos in this family-friendly area.
Skydive Danielson
Catch an event at Skydive Danielson during your trip to Killingly. Take some time to visit the casinos in this family-friendly area.
Bradley Playhouse
6.8/10 (3 reviews)
Enjoy a show at Bradley Playhouse, a storied theater in Putnam. While in this family-friendly area, you can enjoy the restaurants.
Canterbury Green
After visiting Canterbury Green, make a plan to see the other sights and activities in Canterbury. While in this family-friendly area, find time to visit its casinos.
Roseland Cottage
You can study the exhibits at Roseland Cottage, a museum with a storied past, during your travels to Woodstock. Check out the top-notch restaurants or lively bars in this family-friendly area.
Quinebaug Lake State Park
You can take time to visit Quinebaug Lake State Park during your travels to Killingly.
Killingly Pond State Park
7.2/10 (7 reviews)
You can take time to visit Killingly Pond State Park during your travels to Killingly. Discover the waterfalls in this family-friendly area.
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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.
