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 Vermont Inn

The Vermont Inn

3 out of 5
Price was $961, price is now $808 per person
$808
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 free perks like continental breakfast and free self parking.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $5,629, price is now $4,695 per person
$4,695
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This vacation home features laundry facilities. Take advantage of the free self parking.
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $5,166, price is now $4,354 per person
$4,354
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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.
The Vesper

The Vesper

3 out of 5
Price was $1,077, price is now $916 per person
$916
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

Top Windham County hotels deals

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
$92 nightly
The price is $101 total per night
$101 total
Nov 17 - Nov 18
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Breakfast included
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
$91 nightly
The price is $100 total per night
$100 total
Dec 7 - Dec 8
Total with 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.
Pool
Hot Tub
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
$104 nightly
The price is $115 total per night
$115 total
Nov 18 - Nov 19
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
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd West Dover VT
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $126 total per night
$126 total
Nov 17 - Nov 18
Total with taxes and fees
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.
Pool
Pet friendly
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $139 total per night
$139 total
Nov 17 - Nov 18
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
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$162 nightly
The price is $178 total per night
$178 total
Nov 17 - Nov 18
Total with 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.
Pool
Spa
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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 $808. 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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