Deals on vacations and trips to Windham County

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West Dover

Vacations
West Dover

Windham County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $518, price is now $471 per person
$471
per person
Dec 14 - Dec 17
found 13 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $761, price is now $652 per person
$652
per person
Dec 18 - Dec 20
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,280, price is now $1,100 per person
$1,100
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Rutland (RUT)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities 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 $977, price is now $866 per person
$866
per person
Dec 14 - Dec 17
found 13 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $553, price is now $504 per person
$504
per person
Dec 18 - Dec 20
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
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.

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
$99 nightly
The price is $109 total per night
$109 total
Nov 1 - Nov 2
Total with 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 garden, a grocery/convenience store, and a lobby fireplace are also on offer.
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
Free Cancellation
$163 nightly
The price is $179 total per night
$179 total
Nov 9 - Nov 10
Total with taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the gym and perks like free WiFi and a free area shuttle. You'll appreciate the sauna, bar/lounge, and laundry facilities.
Spa
Free WiFi
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
$109 nightly
The price is $120 total per night
$120 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a seasonal outdoor pool and a hot tub. Enjoy the free ski shuttle and onsite ski storage. Enjoy the sauna and perks like free self parking and free WiFi.
Pool
Hot Tub
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $158 total per night
$158 total
Nov 3 - Nov 4
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
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
$144 nightly
The price is $159 total per night
$159 total
Oct 27 - Oct 28
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
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
$111 nightly
The price is $122 total per night
$122 total
Nov 8 - Nov 9
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
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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)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
See properties

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 $471. 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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