Book Exclusive Windham County Vacation Packages

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Autumn colors along Connecticut River, Brattleboro, Vermont

Brattleboro

Vacations
Brattleboro

Windham County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,295, price is now CA $1,066 per person
CA $1,066
per person
Aug 4 - Aug 8
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,517, price is now CA $1,286 per person
CA $1,286
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Chalet 239

Chalet 239

2 out of 5
Price was CA $1,228, price is now CA $1,121 per person
CA $1,121
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was CA $1,350, price is now CA $1,241 per person
CA $1,241
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Rutland (RUT)
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Quechee Gorge Bridge and Wilderness Trails are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $1,289, price is now CA $1,186 per person
CA $1,186
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.

Top Windham County hotels deals

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free cancellation
Reserve now, pay when you stay
The price is CA $189 per night
CA $189
CA $208 total
Jun 30 - Jul 1
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
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
The price is CA $146 per night
CA $146
CA $161 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Pool
Hot tub
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
The price is CA $207 per night
CA $207
CA $248 total
Jul 20 - Jul 21
includes taxes & fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Pool
Hot tub
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
The price is CA $139 per night
CA $139
CA $152 total
Jun 28 - Jun 29
includes taxes & fees
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
Breakfast included
Pet-friendly
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CA $195 per night
CA $195
CA $227 total
Jul 13 - Jul 14
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Parking included
Free WiFi
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
The price is CA $183 per night
CA $183
CA $202 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Breakfast included
Parking 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.

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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 CA $1,066. 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.