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We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!

Brattleboro

Vacations
Brattleboro

Windham County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $553, price is now $433 per person
$433
per person
Nov 22 - Nov 25
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Save 100% on your flight
Price was $771, price is now $556 per person
$556
per person
Dec 9 - Dec 16
found 3 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Save 100% on your flight
Price was $725, price is now $543 per person
$543
per person
Dec 9 - Dec 16
found 3 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Save 100% on your flight
Price was $599, price is now $478 per person
$478
per person
Dec 9 - Dec 16
found 3 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $536, price is now $434 per person
$434
per person
Nov 7 - Nov 10
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.

Top Windham County hotels deals

Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $75 total per night
$75 total
Nov 2 - Nov 3
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A business center, a grocery/convenience store, and a picnic area are also on offer.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $139 total per night
$139 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
$133 nightly
The price is $147 total per night
$147 total
Nov 3 - Nov 4
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $107 total per night
$107 total
Nov 2 - Nov 3
Total with taxes and fees
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $154 total per night
$154 total
Oct 5 - Oct 6
Total with taxes and fees
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $113 total per night
$113 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
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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.

Photos of local treasures

Browse Windham County vacation photos for more inspiration

Southern Vermont showing fall colors and a garden
Southern Vermont which includes a house
Southern Vermont which includes a garden and a house
Southern Vermont showing fall colors
Southern Vermont which includes a river or creek, tranquil scenes and a bridge

Frequently asked questions

How much are vacation packages to Windham County?
Adventure awaits in Windham County, with Travelocity vacation packages starting from as low as $433. Providing both hotels and flights, these amazing deals are a simple way to experience more of our wonderful planet.
Where can I get the best vacation package deals for Windham County?
For the best package deal to Windham County, head straight to Travelocity. Select from 400 airlines and 1,000,000 worldwide properties to create your dream adventure — it's as easy as that.
Why should I purchase my Windham County vacation package with Travelocity?
You'll not only save loads, but you can also access our 24/7 customer support, high-quality service and a Price Match Guarantee. Roam across the globe, discover lesser-known sights and make unforgettable memories — we'll take care of the little details.
Will I save money on my Windham County car rental if I book it with hotels and flights?
You sure can. And our Windham County vacation packages are the ideal way to do it. With just a few clicks you can save money and time by combining your bookings. Pick up the keys to your rental car then set your own course. Looking for things to do? Add some activities or experiences to your package and save on those too.
Which airport is best for Windham County?
That all comes down to where you're leaving from and where you're off to — Albany Intl. Airport (ALB), Manchester-Boston Regional Airport (MHT) or Lebanon Municipal Airport (LEB) are where you'll most likely come in to land.
What is there to do in Windham County?
Windham County boasts hidden gems at every turn, however make sure you plan a trip to Magic Mountain Ski Resort and Lake Raponda during your stay. These two attractions are a must-see.

Where to stay in Windham County: Best areas for travelers

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