Windham County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Bruce Altobelli

Top destinations in Windham County

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Brattleboro

Brattleboro

Top hotels in Windham County

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
The price is 4.859.210 ₫ per night from 19 Jan to 20 Jan
4.859.210 ₫
5.879.644 ₫ total
19 Jan - 20 Jan
includes taxes & fees
7.4/10 Good! (945 reviews)
Place definitely needs some updating but it was clean and the staff was great!

Reviewed on 18 Dec 2025

The Black Bear Lodge at Stratton Mountain Resort
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is 2.210.284 ₫ per night from 13 Jan to 14 Jan
2.210.284 ₫
2.431.312 ₫ total
13 Jan - 14 Jan
includes taxes & fees
7.6/10 Good! (1,002 reviews)
Easy check in and good parking

Reviewed on 9 Jan 2026

The Covered Bridge Inn
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is 8.042.492 ₫ per night from 9 Feb to 10 Feb
8.042.492 ₫
9.625.266 ₫ total
9 Feb - 10 Feb
includes taxes & fees
8.6/10 Excellent! (251 reviews)
Ski on skis off fantastic. Ski valet right on it

Reviewed on 11 Jan 2026

Mount Snow Grand Summit Resort
See all 1,403 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.