Westmoreland Vacation Packages

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Top Westmoreland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $1,381, price is now CA $1,221 per person
CA $1,221
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on Aug. 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $3,248, price is now CA $2,507 per person
CA $2,507
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (806 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was CA $2,911, price is now CA $2,356 per person
CA $2,356
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.6/10 Exceptional! (57 reviews)
Very authentic and comfortable.

Reviewed on Aug. 22, 2025

Chalet 239

Chalet 239

2 out of 5
Price was CA $1,600, price is now CA $1,384 per person
CA $1,384
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (74 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept. The free breakfast was a plus.

Reviewed on Aug. 12, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was CA $1,579, price is now CA $1,457 per person
CA $1,457
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)

Ready to book your vacation to Westmoreland?

 

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Westmoreland Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Sep 4 to Sep 5
CA $172
CA $187 total
Sep 4 - Sep 5
includes taxes & fees
Keene Elm City Hotel, Ascend Hotel Collection
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 31 to Sep 1
CA $154
CA $170 total
Aug 31 - Sep 1
includes taxes & fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug. 22, 2025

Colonial Motel And Spa
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Aug 31 to Sep 1
CA $152
CA $165 total
Aug 31 - Sep 1
includes taxes & fees
Days Inn by Wyndham Keene NH
See all 1,124 properties in Westmoreland
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.
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Frequently asked questions

How much does a Westmoreland vacation package cost?
You'll find cheap prices from CA $1,221 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.