Deals on vacations and trips to Windham County

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A calm lake reflecting a forest with autumn foliage.

Brattleboro

Vacations
Brattleboro

Windham County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Chalet 239

Chalet 239

2 out of 5
Price was $781, price is now $661 per person
$661
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $862, price is now $713 per person
$713
per person
Sep 27 - Oct 2
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,118, price is now $929 per person
$929
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Price was $865, price is now $718 per person
$718
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Springfield (VSF)
This hotel features free WiFi in public areas, wedding services, and free self parking. Enjoy the free ski shuttle and onsite ski storage. Enjoy the free continental breakfast each morning.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,096, price is now $953 per person
$953
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.

Top Windham County hotels deals

Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Aug 23 - Aug 24
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a grocery/convenience store, and a lobby fireplace are also on offer.
Breakfast included
Pet friendly
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $133 total per night
$133 total
Aug 24 - Aug 25
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.
Pet friendly
Parking included
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $127 total per night
$127 total
Sep 8 - Sep 9
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.
Pool
Hot Tub
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
$130 nightly
The price is $142 total per night
$142 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
Free Cancellation
$163 nightly
The price is $179 total per night
$179 total
Sep 21 - Sep 22
Total with taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the gym and perks like free WiFi and a free area shuttle. You'll appreciate the sauna, bar/lounge, and laundry facilities.
Spa
Free WiFi
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
100 Chickering Drive Brattleboro VT
Free Cancellation
$167 nightly
The price is $184 total per night
$184 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
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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.

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

Photos of local treasures

Browse Windham County vacation photos for more inspiration

A wooden covered bridge over a river with stone walls on either side.
A frozen lake with people fishing and walking around.
A wooden cabin with a stone tower, surrounded by snow-covered ground and trees.
A red covered bridge with a sign indicating a legal load limit of 16,000 pounds.
A covered bridge over a river, surrounded by snow-covered landscape and trees.

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 $661. 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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