Book Exclusive Windham County Vacation Packages

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Search vacation packages deals in Windham County's top destinations

A calm lake reflecting a forest with autumn foliage.

Brattleboro

Vacations
Brattleboro

Windham County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,024, price is now CA $896 per person
CA $896
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) 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.
The Landgrove

The Landgrove

3.5 out of 5
Price was CA $1,661, price is now CA $1,297 per person
CA $1,297
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,381, price is now CA $1,141 per person
CA $1,141
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was CA $1,109, price is now CA $964 per person
CA $964
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $1,051, price is now CA $916 per person
CA $916
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.

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
The price is CA $119 per night
CA $119
CA $130 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Breakfast included
Pet-friendly
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
The price is CA $214 per night
CA $214
CA $256 total
Nov 4 - Nov 5
includes taxes & fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Spa
Free WiFi
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
The price is CA $253 per night
CA $253
CA $278 total
Oct 7 - Oct 8
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
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
270 Handle Rd West Dover VT
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
CA $136 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Pool
Hot tub
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
The price is CA $187 per night
CA $187
CA $226 total
Oct 13 - Oct 14
includes taxes & fees
Book a stay at this ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stratton Mountain Resort and Villager Ski Lift are located nearby.
Hot tub
Breakfast included
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free cancellation
The price is CA $159 per night
CA $159
CA $175 total
Nov 1 - Nov 2
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 helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
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)
Hit the slopes in Stratton with a visit to Stratton Mountain Resort. Discover the mountain views in this quaint area.
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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 CA $896. 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.