Windham County Holidays

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  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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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Top destinations in Windham County

Autumn colors along Connecticut River, Brattleboro, Vermont
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Brattleboro

Brattleboro

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Our pick of the best Windham County Hotel Deals

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
The price is NZ$251 per night from 15 Mar to 16 Mar
NZ$251
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (70 reviews)
Great location. Clunky check-in as all virtual. Hot tub, which is the reason booked was broken, saunas did not heat up, could not adjust the heat in the room, so even though we tried to turn it off it was 80’ overnight. Machine for tea also didn’t work. Clean rooms but the hot tub and heat issues ...

Reviewed on 10 Mar 2026

Hideaway Inn Mt. Snow
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is NZ$176 per night from 16 Mar to 17 Mar
NZ$176
16 Mar - 17 Mar
includes taxes & fees
6.8/10 (1,002 reviews)
It was good to have pool option after a ski day

Reviewed on 10 Mar 2026

Colonial Motel And Spa
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
The price is NZ$578 per night from 6 Apr to 7 Apr
NZ$578
6 Apr - 7 Apr
includes taxes & fees
8.6/10 Excellent! (262 reviews)
Staff were all friendly. Room was clean. Food at the resort restaurant was great. We have been stay at this hotel many times in the past but were delighted seeing there are on site EV charging stations now. It is a nice add-on. However, one may be lucky or unlucky to get a charging space when stay ...

Reviewed on 9 Mar 2026

Grand Summit Resort, A Vail Resorts Property
See all 1,410 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.