Windham County Holidays

Photo by Bruce Altobelli

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    Save up to €900 when you book a flight and hotel together*

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

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Top destinations in Windham County

Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak
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Stratton

Stratton

Top hotels in Windham County

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 €119 per night from 7 Jun to 8 Jun
€119
7 Jun - 8 Jun
includes taxes & fees
8.2/10 Very Good! (970 reviews)
Had a great stay, staff friendly. Breakfast, lots of options - simple but great for our family. Everything we needed, we will be back.

Reviewed on 5 May 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is €131 per night from 10 May to 11 May
€131
10 May - 11 May
includes taxes & fees
8.6/10 Excellent! (876 reviews)
Very well run hotel, conveniently located in the heart of Brattleboro. Free parking in a lot next to the hotel was a nice touch. My only gripe would be that my room (104) had no view as the windows were made of some kind of stained glass that you can't see through and couldn't open. Also they could ...

Reviewed on 4 May 2026

Latchis Hotel
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 refundableReserve now, pay when you stay
The price is €134 per night from 13 May to 14 May
€134
13 May - 14 May
includes taxes & fees
8.6/10 Excellent! (268 reviews)
Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful

Reviewed on 2 May 2026

Grand Summit Resort, A Vail Resorts Property
See all 1,402 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.