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.
Deerfield Valley Inn
CA $940
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (128 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
Vikings Villages Resort
CA $1,171
per person
Oct 5 - Oct 8
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (222 reviews)
This resort was amazing! We booked the stay on our way back home from an event in New York. The cabin was comfortable and the property scenic. We wish we had the chance to stay longer, but will definitely be back. The Viking theme was incredible and the attention to detail in our cabin demonstrated the owners knowledge of what travelers need and want. We could not have been happier with our stay. This was more than just a place to sleep as it left us with a lot of good memories.
Reviewed on Aug 16, 2026
Latchis Hotel
CA $1,141
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (945 reviews)
Booked this hotel based on the website photos, but the room was nothing like what we got. It had a persistent musty smell, made worse if we turned off the wobbly pedestal fan that was the only thing airing it out. It was also dusty throughout, the bathroom sink dripped all night because it wouldn’t fully shut off, and the window panes were broken. We also found dead bugs and spiderwebs around the room. Ended up checking out a day early, which wasn’t the plan.
Parking is also a hassle. Only 12(ish) spots on-site, first come first served, in a very tight lot. If those are full, you’re stuck paying hourly at an overflow lot.
Staff at check-in and around the property were genuinely nice, so that’s worth noting. But the room condition didn’t match what was advertised at all. Would not book again based on this experience.
Reviewed on Aug 16, 2026
Windham County Hotel Deals
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $104
CA $114 total
Aug 18 - Aug 19
includes taxes & fees
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $144
CA $159 total
Aug 19 - Aug 20
includes taxes & fees
8.6/10 Excellent! (956 reviews)
"Booked this hotel based on the website photos, but the room was nothing like what we got. It had a persistent musty smell, made worse if we turned off the wobbly pedestal fan that was the only thing airing it out. It was also dusty throughout, the bathroom sink dripped all night because it wouldn’t ..."
Reviewed on Aug 16, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $167
CA $184 total
Sep 9 - Sep 10
includes taxes & fees
8.2/10 Very good! (1,012 reviews)
"Room type was changed from 2 beds to one without notifying me. We went somewhere else"
Reviewed on Aug 17, 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
How much does a Windham County vacation package cost?
Custom build your Windham County package from an affordable CA $940. 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
Stratton Mountain Resort
9.2/10 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
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.
The Stone Church
8.6/10 (39 reviews)
After visiting The Stone Church, make a plan to see the other sights and activities in Brattleboro. While you're here, you can savor the top-notch restaurants.
Magic Mountain Ski Resort
8.6/10 (74 reviews)
Hit the slopes in Londonderry with a visit to Magic Mountain Ski Resort. Discover the mountain views in this quaint area.
Stratton Mountain Summit Gondola
9.4/10 (98 reviews)
Enjoy a trip to Stratton Mountain Summit Gondola and popular activities like skiing in Stratton. Discover the mountain views in this quaint area.
Vermont Country Store
9.2/10 (382 reviews)
Enjoy an outing to Vermont Country Store during your stay in Rockingham. You can seek out the ski slopes while in the area.
Vermont Marketplace
10.0/10 (1 review)
You can browse for the perfect souvenirs at Vermont Marketplace during your visit to Brattleboro. While you're here, you can savor the top-notch restaurants.
Lake Raponda
9.6/10 (10 reviews)
Commune with nature and explore the great outdoors at Lake Raponda during your travels in Wilmington. While you're here, you can savor the top-notch restaurants.
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 $133
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
