Windham County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Windham County

Milford Cityscape in winter over the Wepawaug River with views of the First Church of Christ in Milford built in 1824, stone bridge, and bench at the Lower Lagoon Park green in Connecticut
FlightsFlightsHotelsHotels

Willimantic

Willimantic

Top hotels in Windham County

Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

2.5 out of 5
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
The price is 2.155.519 ₫ per night from 24 Jun to 25 Jun
2.155.519 ₫
2.478.847 ₫ total
24 Jun - 25 Jun
includes taxes & fees
8/10 Very good! (2,770 reviews)
"It was a pleasure to stay here. Thank you!"

Reviewed on 23 Jun 2026

Hilltop Inn and Suites, near Foxwoods Casino
Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton

3 out of 5
55 Whitehall Avenue Mystic CT
Fully refundableReserve now, pay when you stay
The price is 4.428.435 ₫ per night from 1 Jul to 2 Jul
4.428.435 ₫
5.092.700 ₫ total
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very good! (1,688 reviews)
"Great customer service!!!"

Reviewed on 22 Jun 2026

Spark by Hilton Mystic Groton
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

3.5 out of 5
411A & 411B Norwich Westerly Road North Stonington CT
Fully refundableReserve now, pay when you stay
The price is 2.916.935 ₫ per night from 28 Jun to 29 Jun
2.916.935 ₫
4.139.979 ₫ total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,675 reviews)
"The look of the hotel was beautiful. but at the outside seating area there were cigarette butts all over the ground even with receptacles available. I suggest making hotel property smoke free. Also when I checked in the front desk ran my card twice for incidentals (total $300) when i noticed it on ..."

Reviewed on 22 Jun 2026

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
See all 1,199 properties in Windham County
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 holiday package cost?
Discover the best of Windham County from as low as . 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 holiday 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 1null000null000 properties in all corners of the globe, so that everyone has a chance to travel and fulfil those holiday 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 holiday?
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 holiday!
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 holiday 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 holiday package?
You can. We realise even the best-laid plans can fail, so we're happy to help if you have to make changes to your Windham County holiday 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.

Explore a world of travel with Expedia