Windham County Holidays

Photo by Bruce Altobelli

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

A forest with autumn foliage reflecting in a calm lake.
FlightsFlightsHotelsHotels

Stratton

Stratton

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 €112 per night from 9 Aug to 10 Aug
€112
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (945 reviews)
"Main Street Brattleboro so great, near Restaurants and entertainment. We saw a film downstairs, LPs and are Record player in Rooms!"

Reviewed on 3 Aug 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 €124 per night from 12 Aug to 13 Aug
€124
12 Aug - 13 Aug
includes taxes & fees
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is €71 per night from 6 Aug to 7 Aug
€71
6 Aug - 7 Aug
includes taxes & fees
6.8/10 (32 reviews)
"This is a very tired motel. The sign says grand opening, but apparently their grand opening is sometime in the future! Tattered carpets, old drapery, no landscaping to speak of, the lounge area was filled with boxes. The check-in area needed a massive update. Breakfast seemed to have been an afterthought. ..."

Reviewed on 3 Aug 2026

Colonial Motel
See all 1,372 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 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 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

A snow-covered forest with a clear sky.

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.
See properties

What to do in Windham County

Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

€83
per adult
Mindful Forest Escape: Rebalance, reflect and connect
Colonial Flintlock Musket Experience

Colonial Flintlock Musket Experience

€113
per adult
100% of travellers recommend
Colonial Flintlock Musket Experience
See all activities in Windham County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.