Windham County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Bruce Altobelli

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

A river with a bridge, a town, and surrounding hills.
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Brattleboro

Brattleboro
A stone structure with a red and white sign reading 'Stratton' and a bear silhouette.
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Stratton

Stratton

Top Windham County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chalet 239

Chalet 239

2 out of 5
Price was CA $2,808, price is now CA $2,417 per person
CA $2,417
per person
Dec 24 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (157 reviews)

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $3,187, price is now CA $2,488 per person
CA $2,488
per person
Dec 24 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (147 reviews)

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Save 100% on your flight
Price was CA $5,848, price is now CA $4,670 per person
CA $4,670
per person
Dec 24 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (138 reviews)

Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Save 100% on your flight
Price was CA $6,327, price is now CA $5,338 per person
CA $5,338
per person
Dec 24 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (23 reviews)

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $3,885, price is now CA $3,312 per person
CA $3,312
per person
Dec 24 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (324 reviews)

Windham County Hotel Deals

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
The price is CA $227 per night from Nov 17 to Nov 18
CA $227
CA $271 total
Nov 17 - Nov 18
includes taxes & fees
Grand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Dec 11 to Dec 12
CA $118
CA $130 total
Dec 11 - Dec 12
includes taxes & fees
Colonial Motel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Nov 23 to Nov 24
CA $159
CA $175 total
Nov 23 - Nov 24
includes taxes & fees
Latchis Hotel
See all 1,376 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windham County vacation package cost?
Custom build your Windham County package from an affordable CA $2,417. Choose from any combination of flights, hotels and rental cars to put together the escape you've been dreaming about for ages. Remember to add on some tours and experiences!
How do I get a cheap travel package to Windham County?
Think of all the fabulous things you could do in Windham County with extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into a Windham County vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can choose from more than 550 air carriers and 1,000,000 properties throughout the world. Whether you're enjoying a break with the whole family or surprising your special someone, planning a getaway to Windham County is better with a package.
What are the top hotels in Windham County?
When it comes to hotels in Wilmington, Colonial Motel And Spa and Hampton Inn Brattleboro are two popular options. If you're heading to Stratton, The Putney Inn and The Black Bear Lodge at Stratton Mountain Resort look forward to welcoming you.
How far in advance should I book my Windham County vacation?
Reward yourself with the biggest variety and the lowest prices by booking your trip to Windham County nice and early. Airlines tend to release flights around a year before departure, so start your planning ASAP. That said, Expedia is committed 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?
That depends entirely on you. You can pick from a range of Windham County packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your ideal Windham County escape looks like, you'll save!
What should I know before booking a Windham County travel package?
So many places to travel to, so many things to see and do. With a travel package, you'll be able to check more of them off your list. Combine your hotels, rental cars and flights and enjoy big savings.
Can I choose my airline with a Windham County Expedia vacation package?
Yes, and with more than 550 airlines to select from all over the world, you have plenty of choice. Search the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Windham County vacation package?
You sure can, and we'll help you every step of the way. You may be able to change or cancel your Windham County vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, look up our Customer Service Portal for more information.

Stay near popular Windham County attractions

Skiers on a snowy slope with a ski lift in the background.
Photo by Doug Blackmore/Mount Snow
Open Photo by Doug Blackmore/Mount Snow

Mount Snow

9.2/10 (568 reviews)
Perform wild tricks on a world-class terrain park or cruise down scenic blue-graded runs at this Green Mountain ski resort in West Dover.
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What to do in Windham County

Vermont RT 100 App-Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

CA $134
per adult
Mindful Forest Escape: Rebalance, reflect and connect
See all activities in Windham County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.