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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,042, price is now $890 per person
$890
per person
Dec 15 - Dec 19
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $3,419, price is now $2,812 per person
$2,812
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,285, price is now $1,079 per person
$1,079
per person
Dec 15 - Dec 19
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,508, price is now $1,271 per person
$1,271
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,724, price is now $1,460 per person
$1,460
per person
Dec 15 - Dec 19
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services, barbecue grills, and a virtual front desk are also on offer.

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
$84 nightly
The price is $93 total per night
$93 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
$169 nightly
The price is $186 total per night
$186 total
Nov 1 - Nov 2
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
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
$183 nightly
The price is $201 total per night
$201 total
Oct 7 - Oct 8
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
$148 nightly
The price is $162 total per night
$162 total
Oct 14 - Oct 15
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
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
$91 nightly
The price is $100 total per night
$100 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
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
$94 nightly
The price is $103 total per night
$103 total
Oct 25 - Oct 26
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 picnic area is also provided.
Breakfast included
Pet friendly
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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 $890. 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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