Deals on vacations and trips to Windham County

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Windham County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $401, price is now $359 per person
$359
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $460, price is now $397 per person
$397
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Rutland (RUT)
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $419, price is now $364 per person
$364
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $431, price is now $380 per person
$380
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Rutland (RUT)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $462, price is now $414 per person
$414
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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

Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
$68 nightly
The price is $75 total per night
$75 total
Oct 30 - Oct 31
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.
Pool
Breakfast included
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 2 - Oct 3
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Breakfast included
Parking included
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
$150 nightly
The price is $166 total per night
$166 total
Oct 2 - Oct 3
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
$114 nightly
The price is $125 total per night
$125 total
Oct 6 - Oct 7
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.
Pool
Pet friendly
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
$140 nightly
The price is $154 total per night
$154 total
Oct 2 - Oct 3
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.
Pool
Hot Tub
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
$126 nightly
The price is $138 total per night
$138 total
Nov 1 - Nov 2
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
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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 $359. 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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