Windham County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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

Autumn colors along Connecticut River, Brattleboro, Vermont
FlightsFlightsHotelsHotels

Brattleboro

Brattleboro
Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak
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Stratton

Stratton

Windham County Hotel Deals

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jun 7 to Jun 8
CA $174
CA $192 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (976 reviews)
Great staff. Newly updated decor

Reviewed on May 16, 2026

Hampton Inn Brattleboro
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 $177 per night from May 21 to May 22
CA $177
CA $194 total
May 21 - May 22
includes taxes & fees
8.6/10 Excellent! (881 reviews)
Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!

Reviewed on May 15, 2026

Latchis Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
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Colonial Motel And Spa
See all 1,397 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 . 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.