Winhall Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Winhall Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Winhall vacation package. Check out hotels located in Bromley Mountain, which is great for views, families and nature. A trip to Winhall wouldn't be complete without visiting a few major attractions, starting with Stratton Mountain Golf Course. A few quick clicks is all it takes to craft the ultimate Winhall vacation on Expedia.
Top Winhall Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $612, price is now CA $506 per person
CA $506
per person
Aug 31 - Sep 3
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,396 reviews)
Everything was top. Can't think of anything to improve. Hope we can return, certainly we'll try
Reviewed on Jun 22, 2026
Berkshire Mountain Lodge
Price was CA $632, price is now CA $524 per person
CA $524
per person
Aug 31 - Sep 3
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (980 reviews)
Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful staff, great price for a great room( separate dining area, living area, bedroom and huge bathroom!!!!!) extra clean woukd def go back
Reviewed on Jun 21, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $743, price is now CA $621 per person
CA $621
per person
Aug 31 - Sep 3
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (910 reviews)
Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet.
Reviewed on Jun 19, 2026
Best Western Plus Berkshire Hills Inn & Suites
Price was CA $634, price is now CA $545 per person
CA $545
per person
Aug 31 - Sep 3
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The towels and bedding were very nice and the bed was comfortable. There was ample, close parking. However, the sink drain was slow. There was no body wash in the shower. The refrigerator noise was so loud we had to unplug it while we slept. The breakfast was poor (no fruit or meat) and the eggs & biscuits and gravy were barely warm. I would not recommend this hotel.
Reviewed on Jun 17, 2026
The Yankee Inn
Price was CA $693, price is now CA $597 per person
CA $597
per person
Aug 31 - Sep 3
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,016 reviews)
I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here.
Reviewed on Jun 23, 2026
Winhall Hotel Deals
Bromley View Inn
522 VT Route 30 Bondville VT
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 1 to Jul 2
CA $131
CA $144 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (449 reviews)
"Cozy ski lodge with generous-sized, comfortable areas for lounging, visiting, eating, relaxing. Innkeeper was friendly & helpful with tips about things to do in the area. Limited breakfast, but it's only the innkeeper to handle everything. Kudos to her!"
Reviewed on Jun 22, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
The price is CA $282 per night from Jul 1 to Jul 2
CA $282
CA $369 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (850 reviews)
"A little overboard on the pride flags and and pushing the pride stuff on everybody but otherwise a nice place to stay"
Reviewed on Jun 12, 2026
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Fully refundable
The price is CA $160 per night from Jun 28 to Jun 29
CA $160
CA $199 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very good! (945 reviews)
"The floor between the bathroom and the bedroom had huge holes in it, which was dangerous; the bathtub still had soap residue, making it slippery; and the king-sized bed was so worn out that my entire side sagged toward the floor. Let’s just say that for $260 USD, I was really unimpressed—not to mention ..."
Reviewed on Jun 22, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
