Westmoreland 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
Top Westmoreland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow
Price was CA $1,131, price is now CA $1,048 per person
CA $1,048
per person
Aug 24 - Aug 28
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (101 reviews)
There is no staff at the facility but someone is available by text
The common areas were great. I can see how this would be a good communal area to meet others in the busy months or go with a big group of friends. I loved the work from home room. The outdoor areas were really nice too.
Unfortunately the entry keypad into my room was very finicky. It would take me multiple tries each time entering my room to hit the numbers just right. My toilet seat in the bathroom was also completely broken off.
Although my stay was okay, I don't think I would personally stay again.
Reviewed on May 22, 2026
Grand Summit Resort, A Vail Resorts Property
Price was CA $1,260, price is now CA $1,164 per person
CA $1,164
per person
Aug 24 - Aug 28
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.6/10 Excellent! (272 reviews)
All aspects of the property were excellent and well maintained. The food, service, gym, pool all top notch.
Reviewed on Jun 17, 2026
Woodstock Inn & Resort
Price was CA $2,571, price is now CA $2,378 per person
CA $2,378
per person
Aug 24 - Aug 28
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (582 reviews)
If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!
Reviewed on Jun 16, 2026
Westmoreland Hotel Deals
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jun 24 to Jun 25
CA $176
CA $193 total
Jun 24 - Jun 25
includes taxes & fees
8.6/10 Excellent! (905 reviews)
"Love the historical aspects of this place."
Reviewed on Jun 17, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 2 to Jul 3
CA $131
CA $142 total
Jul 2 - Jul 3
includes taxes & fees
7/10 Good! (1,010 reviews)
"Our room smelled like mold, likely because there was a lot of rotting and what looked like mold in the bathroom. The carpets themselves needed to be replaced as they had a musty smell likely from too much moisture or spills. This hotel really needs a lot of work to make it feel inviting. Any fixes ..."
Reviewed on Jun 16, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $216 per night from Jun 22 to Jun 23
CA $216
CA $258 total
Jun 22 - Jun 23
includes taxes & fees
8.6/10 Excellent! (276 reviews)
"All aspects of the property were excellent and well maintained. The food, service, gym, pool all top notch."
Reviewed on Jun 17, 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.
