Windham County Vacation Packages
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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 vacation destinations in Windham County
Woodstock
Top Windham County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Michie House in College Hill - Hostel
College Hill
CA $424
per person
Sep 25 - Sep 27
just found
Roundtrip flight included
Toronto (YTO) to Providence (PVD)
6.4/10 (163 reviews)
Before checking in, I had read reviews saying that there was no toilet paper in the restrooms, but I couldn’t believe it. Unfortunately, it was true—THERE WAS NO TOILET PAPER in the restrooms, and two of the three toilets had signs warning guests not to put toilet paper in them.
I did not see any staff during my four-night stay. There was also a loud motor running throughout the night, which made it difficult to sleep.
My room was clean when I arrived, but no one came to clean the room or provide housekeeping service at any point during my four-night stay.
Reviewed on Aug 10, 2026
Omni Providence Hotel
Downtown Providence
CA $780
per person
Sep 25 - Sep 27
just found
Roundtrip flight included
Toronto (YTO) to Providence (PVD)
9/10 Wonderful! (3,195 reviews)
It is a huge hotel and expensive. One has to pay each time you take out the car. $25 a pop.
No pool and yet it calls itself a resort hotel. Very disappointing and I won't stay here again.
Reviewed on Aug 15, 2026
Colonial Inn Seekonk
CA $688
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Providence (PVD)
8.6/10 Excellent! (1,188 reviews)
When we arrived home after our overnight stay, my husband discovered that he'd left behind his toilettries bag with all his meds in the bathroom. We called the hotel and the staff could not have been nicer or more helpful--they had found the bag and promised to hold it for us, and when my son (who lives in the area) went to pick it up, the staff insisted on calling me to make sure it was ok to give it to him. That kind of customer care is priceless. Thank You Colonial Inn!
Reviewed on Aug 15, 2026
Windham County Hotel Deals
Best Western Mystic Hotel
48 Whitehall Ave Mystic CT
Fully refundableReserve now, pay when you stay
CA $190
CA $219 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (693 reviews)
"Nice hotel, friendly staff"
Reviewed on Aug 15, 2026
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
CA $137
CA $157 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very good! (222 reviews)
"The pool needs to be filled up by the top it was half way empty this time i went , too much chlorine"
Reviewed on Aug 14, 2026
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
CA $110
CA $127 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (2,835 reviews)
"Old place not updated . Pillows so cheap not comfortable."
Reviewed on Aug 15, 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.
Frequently asked questions
How much does a Windham County vacation package cost?
Discover the best of Windham County from as low as CA $424. We offer a great selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.
How do I get a cheap travel package to Windham County?
It's as simple as bundling. Hotels, rental cars and flights — combine whatever you need into a Windham County vacation package and save. Score even more bargains when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your way. We offer over 550 air carriers and 1,000,000 properties in all corners of the globe, so that everyone has a chance to travel and fulfill those vacation dreams.
What are the top hotels in Windham County?
For properties in Ashford with friendly service and comfy beds, check out Quiet Corner Inn and La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino. If you're stopping by Woodstock as well, you can look forward to a wonderful night's sleep at Motel 6 Putnam, CT or Comfort Inn & Suites.
How far in advance should I book my Windham County vacation?
Get rewarded with the widest variety at the cheapest prices by booking your Windham County adventure early. Air carriers usually publish flight tickets anywhere up to 12 months before departure, so secure your spot as soon as possible. Having said that, Expedia is dedicated to giving you the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Windham County travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your perfect Windham County travel package. Once you've made your booking, you can add on the fun stuff like tours and activities. Remember — the more you bundle, the more cash you'll save!
What should I know before booking a Windham County travel package?
So many places to explore, so many things to see and do. With a package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Windham County Expedia vacation package?
Yes, and with more than 550 airlines to pick from across the globe, it's all about choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Windham County vacation package?
You can. We realize even the best-laid plans can fail, so we're happy to help if you have to make changes to your Windham County vacation package. You may be able to amend or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
