Westmoreland Vacation Packages
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Top Westmoreland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
CA $1,405
per person
Nov 25 - Nov 30
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8/10 Very good! (225 reviews)
Great location! But…. Two recommendations.
Property should have been maintained better (we found cockroaches inside coffee machines).
There was no instruction to collect the keys from a different location. Kinda embarrassing.
Reviewed on Oct 17, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $2,213
per person
Nov 25 - Nov 30
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.
Reviewed on Oct 15, 2026
Ready to book your vacation to Westmoreland?
Westmoreland Hotel Deals
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
CA $222
CA $265 total
Nov 4 - Nov 5
includes taxes & fees
8.6/10 Excellent! (324 reviews)
"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward ..."
Reviewed on Oct 20, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $125
CA $138 total
Nov 2 - Nov 3
includes taxes & fees
6.2/10 (103 reviews)
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Reviewed on Oct 20, 2026
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
CA $124
CA $136 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (147 reviews)
"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff ..."
Reviewed on Oct 19, 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.
Frequently asked questions
How much does a Westmoreland vacation package cost?
You'll find cheap prices from CA $1,405 on Expedia for your Westmoreland break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Westmoreland costs.
What are the cheapest months to go to Westmoreland?
January, February and March are the best times to search for cheap Westmoreland vacation packages. Travelling in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Westmoreland?
Generally, a handful of days is enough to visit the major attractions during your Westmoreland vacation. However, if you prefer to have some time to kick back or go on day tours, think about extending your trip.
How to find the best Westmoreland package deals?
Start your search for a Westmoreland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Westmoreland package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Westmoreland escape underway.
Is it cheaper to book a Westmoreland vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your Westmoreland escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Westmoreland?
If you're considering an impromptu Westmoreland getaway, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Westmoreland?
- Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the activities available will also help you decide when to visit Westmoreland.
- Plan your budget wisely: On top of the price of your stay, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Westmoreland.
- Work out your trip length: Think about how much time you want to spend discovering Westmoreland. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Westmoreland vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
