Windham County Holidays

Photo by Bruce Altobelli

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    Save up to S$1,300 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

A mountainous landscape with autumn foliage and a lake.
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Stratton

Stratton
A stream flowing over rocks in a forest with dense green foliage.
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Putney

Putney

Top hotels in Windham County

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 refundable
The price is S$239 per night from 6 Jul to 7 Jul
S$239
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (284 reviews)
"Lovely resort although the pool is closed until October. Beautiful, peaceful property. 300+ rooms! Music on patio with s’mores was fun. Karen was very nice and helpful. Only negative it is 15 miles from town and not a lot to do!"

Reviewed on 29 Jun, 2026

Grand Summit Resort, A Vail Resorts Property
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$141 per night from 7 Jul to 8 Jul
S$141
7 Jul - 8 Jul
includes taxes & fees
8.6/10 Excellent! (918 reviews)
"This hotel is poor. Nothing like the advertisements. It is dingy,dark, noisy. The traffic from outside is overwhelming loud and I was on the quiet side. The bathroom is horrible with no place to put anything. The sink constantly drips. I could not take a shower since there is a column halfway along ..."

Reviewed on 30 Jun, 2026

Latchis Hotel
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 S$185 per night from 16 Jul to 17 Jul
S$185
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"The staff were very professional. Hotel was clean and very nice"

Reviewed on 27 Jun, 2026

Hampton Inn Brattleboro
See all 1,390 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.

Stay near popular Windham County attractions

A snow-covered forest with a clear sky.

Stratton Mountain Resort

9.2/10 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
See properties

What to do in Windham County

Vermont RT 100: Self-Guided Driving Audio Tour

Vermont RT 100: Self-Guided Driving Audio Tour

S$22
per traveller
Vermont RT 100: Self-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

S$123
per adult
Mindful Forest Escape: Rebalance, reflect and connect
Colonial Flintlock Musket Experience

Colonial Flintlock Musket Experience

S$167
per adult
100% of travellers recommend
Colonial Flintlock Musket Experience
See all activities in Windham County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.