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

Chrysanthemums and pumpkins for sale at a farm stand near Woodstock, Connecticut.
FlightsFlightsHotelsHotels

Woodstock

Woodstock

Top Windham County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sea Shell Motel

Sea Shell Motel

2 out of 5
Price was CA $1,856, price is now CA $1,321 per person
CA $1,321
per person
Aug 8 - Aug 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Providence (PVD)
8.2/10 Very Good! (40 reviews)
Owner was great, rooms and bed were comfortable.

Reviewed on May 13, 2026

The Preserve Sporting Club & Resort

The Preserve Sporting Club & Resort

4 out of 5
Price was CA $5,661, price is now CA $3,555 per person
CA $3,555
per person
Aug 8 - Aug 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Providence (PVD)
8.8/10 Excellent! (9 reviews)
The resort itself stood out so beautiful!

Reviewed on Jan 6, 2026

Block Island Beach House

Block Island Beach House

3.5 out of 5
Price was CA $4,997, price is now CA $3,345 per person
CA $3,345
per person
Aug 5 - Aug 12
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to Providence (PVD)
8.4/10 Very Good! (381 reviews)
Wonderful time. Very comfortable bed.

Reviewed on Dec 2, 2025

Wayfinder Newport

Wayfinder Newport

4 out of 5
Price was CA $3,193, price is now CA $2,260 per person
CA $2,260
per person
Aug 5 - Aug 12
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to Providence (PVD)
8.2/10 Very Good! (1,007 reviews)
Clean room. Nice space. Good location. Convenient shuttle!

Reviewed on May 7, 2026

Pleasant View Inn

Pleasant View Inn

3 out of 5
Price was CA $2,448, price is now CA $1,741 per person
CA $1,741
per person
Aug 8 - Aug 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Providence (PVD)
8/10 Very Good! (1,001 reviews)
The room was lovely, the view was amazing! The restaurant was wonderful!

Reviewed on May 15, 2026

Windham County Hotel Deals

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 CA $115 per night from Jun 8 to Jun 9
CA $115
CA $132 total
Jun 8 - Jun 9
includes taxes & fees
8/10 Very Good! (2,733 reviews)
Shuttle service to Foxwoods was a plus!

Reviewed on May 15, 2026

Hilltop Inn and Suites, near Foxwoods Casino
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 CA $107 per night from May 27 to May 28
CA $107
CA $165 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (2,636 reviews)
We stay here everytime we visit Mystic, CT. Always a lovely experience.

Reviewed on May 15, 2026

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from May 28 to May 29
CA $141
CA $162 total
May 28 - May 29
includes taxes & fees
9.2/10 Wonderful! (2,677 reviews)
We stayed two nights in room 313. The whole trip the room temp was 74. We talked to the desk they sent someone to fix it. The person changed the filters and said it would be better. We left the room temp it was still 74. My hubby slept above the sheets due to being hot. Totally not happy with this ...

Reviewed on May 16, 2026

Hyatt Place Uncasville - Casino Area
See all 1,213 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.
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Frequently asked questions

How much does a Windham County vacation package cost?
Discover the best of Windham County from as low as CA $1,321. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.