Windham County Vacations & Trips from $780
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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
Willimantic
Woodstock
Plainfield
Putnam
Thompson
Brooklyn
Dayville
Pomfret
Ashford
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Beatrice
Downtown Providence
$933
per person
Dec 11 - Dec 15
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
9.8/10 Exceptional! (603 reviews)
The Beatrice was a wonderful place to stay - the beds were comfortable, amenities great, and the staff very friendly and helpful. Highly recommended.
Reviewed on Sep 28, 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
$93 nightly
$107 total
Oct 4 - Oct 5
Total with taxes and fees
8.4/10 Very Good! (668 reviews)
"Everything was really clean"
Reviewed on Sep 28, 2026
The Fox Tower at Foxwoods
350 Trolley Line Blvd Mashantucket CT
$160 nightly
$184 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (1,288 reviews)
"Check in was very slow; many stations, not many people to staff them."
Reviewed on Sep 28, 2026
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
$93 nightly
$107 total
Sep 29 - Sep 30
Total with taxes and fees
7.8/10 Good! (2,898 reviews)
"Breakfast area very clean"
Reviewed on Sep 28, 2026
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.
Killingly Shopping Center
8.2/10 (13 reviews)
You can find the perfect gifts to bring home at Killingly Shopping Center during your stay in Killingly. Take some time to visit the casinos in this family-friendly area.
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 lively bars or top-notch restaurants in this quaint area.
Woodstock Golf Course
Enjoy a round of golf in Woodstock at Woodstock Golf Course. Check out the top-notch restaurants or lively bars in this quaint 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.
Moosup Pond Beach
8.0/10 (2 reviews)
Why not spend a lazy afternoon at Moosup Pond Beach during your trip to Moosup? While you're in the area, wander around the parks.
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.
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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.
