Windham County Vacation Packages 2025/2026 from $563

Search vacation packages deals in Windham County's top destinations

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!

Brattleboro

Vacations

Windham County flight + hotel vacation packages

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

Mountaineer Inn

per person

Jul 25 - Jul 28

found 4 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

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.

The Shire Woodstock

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Chateau Rooms

per person

Aug 28 - Sep 2

found 6 hours ago

Roundtrip flight included

New York (NYC) to Rutland (RUT)

This smoke-free guesthouse features a full-service spa and a restaurant. A convenience store and wedding services are also provided.

Winterplace at Okemo

Clock Tower Base Area

per person

Jul 25 - Jul 28

found 4 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.

Jackson Gore Village

Jackson Gore Base Area

per person

Jul 25 - Jul 28

found 4 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

Top Windham County hotels deals

Colonial Motel And Spa

889 Putney Rd, Brattleboro, VT

Free Cancellation

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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

1378 Putney Road, Brattleboro, VT

Free Cancellation

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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

1186 Putney Road, Brattleboro, VT

Free Cancellation

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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

50 Main Street, Brattleboro, VT

Free Cancellation

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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 Covered Bridge Inn

1043 Putney Road, Brattleboro, VT

Free Cancellation

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This hotel features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning.

Breakfast included

Parking included

Holiday Inn Express Hotel & Suites Brattleboro by IHG

100 Chickering Drive, Brattleboro, VT

Free Cancellation

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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.

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Southern Vermont showing fall colors and a garden

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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 $563. 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

West Dover: This place is an art lover's paradise, with lots of exciting attractions to explore. Start your sightseeing at Lost Nation Theater or at T.W. Wood Gallery. If you'd like to see even more creativity, plan an outing to T.W. Wood Art Gallery too. Consider comfortable stays like the 5 Miles From Mount Snow - Hot Tub - Rec Room - Fireplace, the Vermont Mt. Snow Vacation Home W/game Room and the New to Market, Private Home, Mount Snow Village, Hermitage.
Brattleboro: It'll be tricky deciding which of the many attractions to explore here first. Start with Marlboro Music Festival, Brattleboro Farmers' Market and The Stone Church. If you've still got time on your hands, head on over to Brattleboro Bowl and Brattleboro Common. Want to know where to get a superb night's sleep? The Latchis Hotel, The Historic Latchis Hotel and Theatre and the Econo Lodge Brattleboro are our favorites.
Wilmington: Stay someplace comfortable like the White House Inn and then get ready to discover this buzzing destination's many attractions. The Hermitage Golf Club, Adams Family Farm and Lake Raponda are some you won't want to miss. If you need more hotel options, check out the rates at the Beautiful Country Getaway Near Downtown Wilmington! and the Nordic Hills Lodge.
Stratton: If it's your first time in Stratton and you're after some suggestions on where to stay, the Slopeside G Unit Ski On Ski Off, the Stratton SKI In/out ALL NEW Kitchen and Bathrooms!! and The Black Bear Lodge at Stratton Mountain Resort are terrific choices. What's more, they're great bases to explore this destination's numerous attractions. Stratton Mountain Resort, American Express Ski Lift and Stratton Mountain Summit Gondola Ski Lift are favorites of travelers and locals alike. Be sure to visit other sights like Solstice Ski Lift, Villager Ski Lift and Snow Bowl Ski Lift.
South Londonderry: A Windham County vacation just isn't the same without a visit to Magic Mountain Ski Resort. Book a room at the Baby Barn, Architect Owner or the Beautifully Maintained Custom Built Home on 7 Acres - 3 mi From Stratton Access and you'll be able to head there whenever you feel like it.