Deals on vacations and trips to Windham County

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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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $618, price is now $492 per person
$492
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $698, price is now $583 per person
$583
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
The One Cat B&B

The One Cat B&B

2.5 out of 5
Price was $643, price is now $554 per person
$554
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A communal living room, a library, and luggage storage are also on offer.
Pond View Cabin in Chittenden

Pond View Cabin in Chittenden

2 out of 5
Price was $1,251, price is now $1,099 per person
$1,099
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $2,457, price is now $2,204 per person
$2,204
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
This vacation home features laundry facilities. Take advantage of the free self parking.

Top Windham County hotels deals

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
$188 nightly
The price is $206 total per night
$206 total
Jan 26 - Jan 27
Total with taxes and fees
This smoke-free resort's 10 restaurants, 2 bars/lounges, and hot tub are some of the featured amenities. There's a free ski shuttle, and ski passes and ski storage are available on site. Families will appreciate the arcade/game room, kid-friendly dining, and supervised childcare.
Hot Tub
Breakfast included
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$333 nightly
The price is $366 total per night
$366 total
Feb 9 - Feb 10
Total with taxes and fees
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
Pool
Hot Tub
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
$84 nightly
The price is $93 total per night
$93 total
Jan 11 - Jan 12
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Parking included
Free WiFi
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $128 total per night
$128 total
Jan 11 - Jan 12
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
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $136 total per night
$136 total
Jan 12 - Jan 13
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
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $103 total per night
$103 total
Jan 26 - Jan 27
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 picnic area is also provided.
Breakfast included
Pet friendly
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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 $492. 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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