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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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

The Shire Woodstock

3 out of 5
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Houston (IAH) 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.
The Vermont Inn

The Vermont Inn

3 out of 5
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Houston (IAH) to Rutland (RUT)
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the sauna and perks like free self parking and free WiFi.
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Houston (IAH) to Rutland (RUT)
A seasonal outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden and a picnic area are also provided.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Houston (IAH) to Springfield (VSF)
This inn features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning. A fireplace in the lobby and a picnic area are also provided.

Top Windham County hotels deals

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $154 total per night
$154 total
Aug 19 - Aug 20
Total includes 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
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
Free Cancellation
$143 nightly
The price is $157 total per night
$157 total
Aug 28 - Aug 29
Total includes taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $135 total per night
$135 total
Sep 2 - Sep 3
Total includes 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.
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
$138 nightly
The price is $151 total per night
$151 total
Aug 26 - Aug 27
Total includes 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
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$138 nightly
The price is $152 total per night
$152 total
Sep 8 - Sep 9
Total includes 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.
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
$140 nightly
The price is $153 total per night
$153 total
Aug 21 - Aug 22
Total includes 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
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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 $452. 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