Windham County Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

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

Top destinations in Windham County

A beautiful 3 mile hike to the Hamilton Falls in Jamaica State Park is well worth the trip. Such a peaceful experience and great camping in the campground. Other hiking options close by also.
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Jamaica

Jamaica

Windham County Hotel Deals

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 ￥12,302 per night from Dec 14 to Dec 15
￥12,302
￥13,532 total
Dec 14 - Dec 15
includes taxes & fees
7.6/10 Good! (1,001 reviews)
Room very nice, comfortable clean

Reviewed on Nov 29, 2025

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 ￥22,243 per night from Dec 28 to Dec 29
￥22,243
￥24,468 total
Dec 28 - Dec 29
includes taxes & fees
8.2/10 Very Good! (925 reviews)
Convenient, clean. Staff was very friendly and helpful. Close to Highway. Keys weren’t working when we returned from a long day out. TV was also not working, but luckily we were in the room for only a short time before heading out for dinner.

Reviewed on Dec 8, 2025

Hampton Inn Brattleboro
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is ￥24,027 per night from Dec 10 to Dec 11
￥24,027
￥28,757 total
Dec 10 - Dec 11
includes taxes & fees
8.6/10 Excellent! (243 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

Mount Snow Grand Summit Resort
See all 1,364 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.