Windham County Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

    • Better together

    Save up to ฿4,531 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

FlightsFlightsHotelsHotels

Brattleboro

Brattleboro

Top hotels in Windham County

Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is ฿4,691 per night from 31 Oct to 1 Nov
฿4,691
฿5,418 total
31 Oct - 1 Nov
includes taxes & fees
8.6/10 Excellent! (531 reviews)
Clean, quiet and safe. The only issue was finding parking spot in the premises at late night.

Reviewed on 13 Oct 2025

Mountaineer Inn
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 ฿3,080 per night from 2 Nov to 3 Nov
฿3,080
฿3,388 total
2 Nov - 3 Nov
includes taxes & fees
7.6/10 Good! (1,020 reviews)
Very clean besides mold on shower, just needs to be scrubbed with bleach.

Reviewed on 12 Oct 2025

The Covered Bridge Inn
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ฿4,573 per night from 2 Nov to 3 Nov
฿4,573
฿5,031 total
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (803 reviews)
Very cool historical hotel and friendly staff. I want to see a movie in the theater next time. Some details were off, such as no working needle on the record player and tv display settings were messed up, and a broken marble top on the radiator.

Reviewed on 13 Oct 2025

Latchis Hotel
See all 1,340 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.