Deals on vacations and trips to Winhall

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Winhall flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $568, price is now $422 per person
$422
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
The Whitlock

The Whitlock

2 out of 5
Save 100% on your flight
Price was $751, price is now $530 per person
$530
per person
Oct 2 - Oct 5
found 16 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $590, price is now $425 per person
$425
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
Price was $558, price is now $447 per person
$447
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Berkshires Untold

Berkshires Untold

3.5 out of 5
Price was $776, price is now $637 per person
$637
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Top Winhall hotels deals

Bromley View Inn

Bromley View Inn

3.5 out of 5
522 VT Route 30 Bondville VT
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $93 total per night
$93 total
Aug 20 - Aug 21
Total with taxes and fees
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a lobby fireplace, and express check-out are also on offer.
Breakfast included
Pet friendly
Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet

Winhall VT
Get rates
Ski-in/ski-out access and a hot tub are featured at this smoke-free chalet. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. Enjoy the sauna and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Free Cancellation
$257 nightly
The price is $283 total per night
$283 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Pool
Pet friendly
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $217 total per night
$217 total
Aug 24 - Aug 25
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Pool
Hot Tub
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
$164 nightly
The price is $181 total per night
$181 total
Sep 15 - Sep 16
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
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Free Cancellation
$116 nightly
The price is $128 total per night
$128 total
Sep 7 - Sep 8
Total with taxes and fees
This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.
Pool
Hot Tub
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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 Winhall attractions

Stratton Mountain Golf Course

10.0/10 (1 review)
Play a round of golf at Stratton Mountain Golf Course and enjoy other activities in Winhall such as skiing. Discover the mountain views in this quaint area.
See properties

Frequently asked questions

How much are vacation packages to Winhall?
You might be pleasantly surprised — you could find yourself in Winhall for a paltry $422. Here at Travelocity, we save you time and money with our excellent vacation packages. With hotels, flights and experiences all ready to be snapped up, why put it off?
How long should my Winhall vacation be?
Most visitors vacation in Winhall for about 3 nights. That being said, travel is all about uncovering hidden gems and creating cherished memories — why not stay a couple of extra nights so you can do just that?
Where can I get the best vacation package deals for Winhall?
With around 400 airline partners and 1,000,000 hotels across the world, it's hard to top Travelocity. Make the most of our comprehensive range and grab an affordable Winhall vacation package. Doesn't it feel amazing when organizing a trip is that easy?
Why should I purchase my Winhall vacation bundle via Travelocity?
Because we believe in crafting special travel experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our support team is on hand 24/7 to ensure you'll never roam alone. We also have an amazing Price Match Guarantee, so you can lock in your vacation knowing you've landed the best deal possible. If you find a lower price, we'll match it!
Will I save money on my Winhall car rental if I book it with my hotel or flight?
Definitely. And our Winhall vacation packages are the ideal way to do it. With just a few clicks you can save money as well as time by combining your bookings. Collect the keys to your rental car then set your own course. Need to fill your itinerary? Add a few tours to your package and make savings on those too.
Where should I stay when visiting Winhall?
Many people opt to stay at the Bromley View Inn. It's sure to be a great base for your Winhall escape.

Photos of local treasures

Browse Winhall vacation photos for more inspiration

A calm lake surrounded by autumn-colored trees and a clear sky.
A sunset over a mountainous landscape with rocky outcrops and dense forest.