Windham County Holidays
Book a Hotel + Flight or Car together to unlock savings
Top destinations in Windham County
Top hotels in Windham County
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
4.371.660 ₫
4.808.827 ₫ total
1 Oct - 2 Oct
includes taxes & fees
8.6/10 Excellent! (974 reviews)
"Great place. Staff are very nice and helpful."
Reviewed on 1 Sept 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
4.115.095 ₫
4.924.999 ₫ total
7 Sept - 8 Sept
includes taxes & fees
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
2.168.231 ₫
2.385.053 ₫ total
6 Sept - 7 Sept
includes taxes & fees
6.8/10 (48 reviews)
"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."
Reviewed on 31 Aug 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 holiday 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 holiday 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 1null000null000 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 holiday?
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 holiday!
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 holiday 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 holiday 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 holiday 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)
Hit the slopes in Stratton with a visit to Stratton Mountain Resort. Discover the mountain views in this quaint area.
Photo by Doug Blackmore/Mount Snow
Mount Snow
9.2/10 (568 reviews)
Hit the slopes in West Dover with a visit to Mount Snow. Discover the area's mountain views and top-notch restaurants.
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 savour 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.
Vermont Marketplace
10.0/10 (1 review)
You can search for that perfect souvenir at Vermont Marketplace during your trip to Brattleboro. While you're here, you can savour the top-notch restaurants.
Stratton Mountain Summit Gondola
9.4/10 (98 reviews)
Enjoy a trip to Stratton Mountain Summit Gondola and popular activities such as 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.
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 savour the top-notch restaurants.
