Deals on vacations and trips to Windham County

Save when you book Windham County, VT package deals

Choose two or more items and save on your trip:

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
Brattleboro

Windham County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $656, price is now $508 per person
$508
per person
Apr 10 - Apr 13
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,056, price is now $910 per person
$910
per person
Apr 10 - Apr 13
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $680, price is now $603 per person
$603
per person
Apr 10 - Apr 13
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $936, price is now $836 per person
$836
per person
Apr 10 - Apr 13
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $625, price is now $559 per person
$559
per person
Apr 10 - Apr 13
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Top Windham County hotels deals

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
$192 nightly
The price is $211 total per night
$211 total
Mar 3 - Mar 4
Total with taxes and fees
This smoke-free resort's 10 restaurants, 2 bars/lounges, and hot tub are some of the featured amenities. There's a free ski shuttle, and ski passes and ski storage are available on site. Families will appreciate the arcade/game room, kid-friendly dining, and supervised childcare.
Hot Tub
Breakfast included
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$346 nightly
The price is $380 total per night
$380 total
Mar 4 - Mar 5
Total with taxes and fees
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
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
$123 nightly
The price is $135 total per night
$135 total
Mar 16 - Mar 17
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
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $125 total per night
$125 total
Mar 1 - Mar 2
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
Big Bears Lodge

Big Bears Lodge

3 out of 5
344 Route 100 West Dover VT
$178 nightly
The price is $196 total per night
$196 total
Feb 23 - Feb 24
Total with taxes and fees
This bed & breakfast features a seasonal outdoor pool and a hot tub. Free perks include cooked-to-order breakfast, free self parking, and a ski shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Pool
Hot Tub
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
$445 nightly
The price is $503 total per night
$503 total
Mar 3 - Mar 4
Total with taxes and fees
A golf course, 10 restaurants, and 2 indoor tennis courts are all featured at this smoke-free aparthotel. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windham County
View all properties
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

New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont. #InStone
New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont. #InStone
We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
Tiny resort for winter sports
So many beautiful bridges in Vermont! The red details on this one really make it pop. It’s about 30min from Brattleboro, if you are visiting the area. #vermont #coveredbridges #newengland

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 $508. 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

Explore More Ways to Travel with Travelocity