Windham County Vacation Packages
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Your Windham County Vacation
Answer the call of adventure with a tailor-made vacation package to Windham County. Wherever it is you're going and whatever you plan to do, prepare to discover a destination with plenty to offer. Kick off your trip to Windham County with a couple of nights in Wilmington visiting popular attractions like Mount Snow and Mount Snow Golf Course. Londonderry is another city that draws crowds from near and far. Magic Mountain Ski Resort and Jamaica State Park are two of the leading places to see in this destination. From the moment you book your Windham County vacation to when you get back home, Expedia has your back every step of the way.
Top vacation destinations in Windham County
Brattleboro
Stratton
Top Windham County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,502, price is now CA $1,264 per person
CA $1,264
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Property beautiful.
Rooms very large.
Staff very friendly.
The only thing that was odd to me was none of our closets had rods to hang clothes on. We were going to a formal wedding, my husband had a suit and I had a long dress to hang up, but the closets had no rods, and we had 3 closets in our room.
Had to hang the suit from a door handle and the long dress from the shower rod!
Reviewed on Jun 28, 2026
The Shire Woodstock
Price was CA $2,698, price is now CA $2,097 per person
CA $2,097
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (944 reviews)
Lovely place. We stayed in room 118 with our Lab. It was ideal. Recently updated. Loved looking out over the river and ate our dinner and sipped wine on the deck. Great location for exploring Woodstock. Would return in a heart beat.
Reviewed on Jul 1, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,902, price is now CA $1,591 per person
CA $1,591
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Windham County Hotel Deals
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $219 per night from Jul 6 to Jul 7
CA $219
CA $262 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (284 reviews)
"Lovely resort although the pool is closed until October. Beautiful, peaceful property. 300+ rooms! Music on patio with s’mores was fun. Karen was very nice and helpful. Only negative it is 15 miles from town and not a lot to do!"
Reviewed on Jun 29, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Jul 4 to Jul 5
CA $152
CA $167 total
Jul 4 - Jul 5
includes taxes & fees
8.6/10 Excellent! (918 reviews)
"This hotel is poor. Nothing like the advertisements. It is dingy,dark, noisy. The traffic from outside is overwhelming loud and I was on the quiet side. The bathroom is horrible with no place to put anything. The sink constantly drips. I could not take a shower since there is a column halfway along ..."
Reviewed on Jun 30, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Jul 12 to Jul 13
CA $195
CA $214 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"The staff were very professional. Hotel was clean and very nice"
Reviewed on Jun 27, 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
Stay near popular Windham County attractions
What to do in Windham County
Vermont RT 100 App-Guided Driving Audio Tour
CA $24
per traveller
Mindful Forest Escape: Rebalance, reflect and connect
CA $131
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
