Windham County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Bruce Altobelli

Top destinations in Windham County

Autumn colors along Connecticut River, Brattleboro, Vermont
FlightsFlightsHotelsHotels

Brattleboro

Brattleboro

Top hotels in Windham County

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is 3.880.399 ₫ per night from 8 Jun to 9 Jun
3.880.399 ₫
4.268.255 ₫ total
8 Jun - 9 Jun
includes taxes & fees
8.6/10 Excellent! (892 reviews)
"The front desk staff was courteous and the cheese platter at Sage was excellent."

Reviewed on 3 Jun 2026

Latchis Hotel
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 3.217.122 ₫ per night from 14 Jun to 15 Jun
3.217.122 ₫
3.538.834 ₫ total
14 Jun - 15 Jun
includes taxes & fees
8.2/10 Very Good! (989 reviews)
"We had a reat stay. Hotel was vey clean and staff was. Very helpful"

Reviewed on 1 Jun 2026

Hampton Inn Brattleboro
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
Fully refundable
The price is 4.061.030 ₫ per night from 8 Jun to 9 Jun
4.061.030 ₫
4.860.176 ₫ total
8 Jun - 9 Jun
includes taxes & fees
8.6/10 Excellent! (270 reviews)
"It’s a nice resort"

Reviewed on 1 Jun 2026

Grand Summit Resort, A Vail Resorts Property
See all 1,377 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.

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.