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.
Hotel Providence
Downtown Providence
CA $1,854
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Moncton (YQM) to Providence (PVD)
8.4/10 Very good! (1,006 reviews)
I would definitely stay here again. It is in the heart of downtown and a very nice hotel. The room was perfect for us. It is across the street from a church that provides food for the unhoused population, but they didn't bother us. I felt comfortable walking around at night and during the day.
Reviewed on Sep 29, 2026
The Underwood-Hale House
College Hill
CA $2,055
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Moncton (YQM) to Providence (PVD)
9.6/10 Exceptional! (128 reviews)
The aprtment is very clean, excellently appointed, and decorated with considerable charm. I would be happy living there long term! I found communication with the hosts very easy and responses were immediate and helpful. They let us leave our car there while we did a Brown University tour (the University is only 10 min walk away at most). Shopping is available close by and Hazel Origin is an excellent coffee shop. Very great stay!
Reviewed on Sep 30, 2026
The Beatrice
Downtown Providence
CA $2,606
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Moncton (YQM) to Providence (PVD)
9.8/10 Exceptional! (612 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
Windham County Hotel Deals
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
CA $122
CA $140 total
Oct 1 - Oct 2
includes taxes & fees
8.4/10 Very good! (688 reviews)
"The front desk staff was very accommodating."
Reviewed on Sep 30, 2026
The Fox Tower at Foxwoods
350 Trolley Line Blvd Mashantucket CT
Fully refundableReserve now, pay when you stay
CA $183
CA $251 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (1,293 reviews)
"We enjoyed our stayed everything was great."
Reviewed on Sep 29, 2026
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
CA $126
CA $145 total
Oct 1 - Oct 2
includes taxes & 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.
Frequently asked questions
How much does a Windham County vacation package cost?
Discover the best of Windham County from as low as CA $1,854. 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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
