Windham County Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

Photo by Bruce Altobelli

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Windham County

Small waterfalls in a woodland stream surrounded by mossy rocks
FlightsFlightsHotelsHotels

Putney

Putney

Windham County Hotel Deals

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is NT$4,256 per night from Jun 16 to Jun 17
NT$4,256
NT$4,682 total
Jun 16 - Jun 17
includes taxes & fees
8.6/10 Excellent! (901 reviews)
"This truly a gem! One of two remaining historic hotels in Detroit, everything about this hotel was something special. The room was spacious and creatively decorated with a large selection of LP's in the hallway. This also included a record player. The queen size beds were extremely comfortable. The ..."

Reviewed on 2026/6/12

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 NT$3,999 per night from Jul 2 to Jul 3
NT$3,999
NT$4,399 total
Jul 2 - Jul 3
includes taxes & fees
8.2/10 Very Good! (992 reviews)
"Amazing stay! Loved this place!"

Reviewed on 2026/6/13

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 NT$4,843 per night from Jun 22 to Jun 23
NT$4,843
NT$5,796 total
Jun 22 - Jun 23
includes taxes & fees
8.6/10 Excellent! (273 reviews)
"Beautiful property! No breakfast there or coffee cups at the coffee station (had to bring your cups from your room). Had some kids running up and down the halls til about 11:00 pm, but that’s on the parents not the hotel."

Reviewed on 2026/6/15

Grand Summit Resort, A Vail Resorts Property
See all 1,383 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 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.

Stay near popular Windham County attractions

www.alamy.com

Stratton Mountain Resort

9.2/5 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.