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

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.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was CA $1,892, price is now CA $1,585 per person
CA $1,585
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (130 reviews)
Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps

Reviewed on Oct 8, 2026

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $2,178, price is now CA $1,746 per person
CA $1,746
per person
Dec 29 - Jan 4
found 1 day 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
Price was CA $3,978, price is now CA $3,219 per person
CA $3,219
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (138 reviews)

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was CA $2,620, price is now CA $2,174 per person
CA $2,174
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.8/10 Excellent! (1,004 reviews)
We booked a deluxe suite, and it was fantastic — basically a full one-bedroom apartment with a kitchen equipped with all the essentials, including a washing machine and dryer. The location is quiet and peaceful, and the property itself is clean, cozy, and well-maintained. The hotel also has great amenities like a pool, gym, and hot tub — unfortunately, we didn't get a chance to use them this time, but it's a wonderful bonus to have! There were only two small issues: it was a bit tricky to find our room at first since it was located in the far wing of the building, and the heater was rather hard to adjust. Aside from that, our stay was wonderful. We love staying at this hotel and will definitely be back again!

Reviewed on Nov 14, 2026

Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was CA $4,700, price is now CA $4,022 per person
CA $4,022
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (23 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 16 to Nov 17
CA $227
CA $272 total
Nov 16 - Nov 17
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 Nov 20 to Nov 21
CA $118
CA $130 total
Nov 20 - Nov 21
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
8.6/10 Excellent! (1,001 reviews)
"The property was a restored authentic theatre that also had a hotel attached to it. While I can appreciate the fact that it was a historical building, I cannot get past the old, stained, grungy carpet, and the dark, creepy bathroom with exposed plumbing. The hot water took forever to come and our ..."

Reviewed on Nov 14, 2026

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.
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Frequently asked questions

How much does a Windham County vacation package cost?
Custom build your Windham County package from an affordable CA $1,585. 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.