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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $398, price is now $338 per person
$338
per person
Oct 23 - Oct 25
found 15 hours ago
Roundtrip flight included
Orlando (MCO) 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.
The Whitlock

The Whitlock

2 out of 5
Price was $564, price is now $463 per person
$463
per person
Oct 23 - Oct 25
found 15 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $848, price is now $733 per person
$733
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and concierge services.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $428, price is now $371 per person
$371
per person
Oct 23 - Oct 25
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $494, price is now $429 per person
$429
per person
Oct 25 - Oct 28
found 6 hours ago
Roundtrip flight included
Dallas (DFW) 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.

Top Winhall hotels deals

Bromley View Inn

Bromley View Inn

3.5 out of 5
522 VT Route 30 Bondville VT
Get rates
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
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
Oct 20 - Oct 21
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 Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $141 total per night
$141 total
Sep 22 - Sep 23
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$113 nightly
The price is $123 total per night
$123 total
Oct 21 - Oct 22
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $201 total per night
$201 total
Sep 30 - Oct 1
Total with taxes and fees
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
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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 $338. 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.