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
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Brattleboro

Brattleboro

Top hotels in Windham County

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
6.8/10 (1,003 reviews)
Awesome and clean and quiet love the staff

Reviewed on 14 Apr 2026

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Colonial Motel And Spa
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 1.877.300 ₫ per night from 22 Apr to 23 Apr
1.877.300 ₫
2.065.030 ₫ total
22 Apr - 23 Apr
includes taxes & fees
7.6/10 Good! (1,001 reviews)
The rrooms were clean, shower was great. Hallways dark, parking lot not to much lighting. There is no breakfast just coffee.

Reviewed on 29 Mar 2026

The Covered Bridge Inn
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 3.243.138 ₫ per night from 27 Apr to 28 Apr
3.243.138 ₫
3.567.452 ₫ total
27 Apr - 28 Apr
includes taxes & fees
8.2/10 Very Good! (963 reviews)
The construction right below our room until after 9:30pm was aweful. I'm surprised we weren't at least placed in a room further from the construction. Hot tub was brown, not at all like the photos. The room was clean so that met expectations.

Reviewed on 17 Apr 2026

Hampton Inn Brattleboro
See all 1,359 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.