Windham County Vacations & Trips from $796
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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
Dayville
Ashford
Pomfret
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pleasant View Inn
Misquamicut
$7,804
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Providence (PVD)
8.2/10 Very Good! (1,008 reviews)
Great location, right off the beach and a pool. Restaurant at hotel was great too.
Reviewed on Aug 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
Best Western Mystic Hotel
48 Whitehall Ave Mystic CT
Fully refundableReserve now, pay when you stay
$149 nightly
$171 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (722 reviews)
"This a a great hotel at a reasonable price. Right down the street from the aquarium, and a short drive into downtown Mystic. The pool was nice, but the grounds around the pool were a bit overgrown. Rooms are clean and the staff was friendly and knowledgeable."
Reviewed on Aug 28, 2026
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$99 nightly
$114 total
Sep 1 - Sep 2
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 10 - Sep 11
Total with taxes and fees
7.8/10 Good! (2,849 reviews)
"This is the second time we stayed at Hilltop. Hotel is immaculate.....staff accommodating and weekend shuttle is so convenient . You won't be sorry if you choose here. Breakfast is filling and something for everyone! Thank You! My only suggestion is maybe a repeat customer should get a little bit ..."
Reviewed on Aug 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.
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.
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.
Quaddick Reservoir
Commune with nature and explore the great outdoors at Quaddick Reservoir during your travels in Thompson.
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.
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.
