Westmoreland Vacations from $703

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The Latest Westmoreland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $864, price is now $703 per person
$703
per person
Feb 19 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
First room we checked into was not cleaned but staff was quick to get us a new room. New room had a great view of the river and was clean enough. We only had about half a roll of toilet paper in the family room and no spares. Also no phone in the room to call the office. A good place to lay your head but not much more.

Reviewed on Jan 11, 2026

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $3,397, price is now $2,840 per person
$2,840
per person
Feb 12 - Feb 16
found 2 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
8/10 Very Good! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,483, price is now $1,339 per person
$1,339
per person
Feb 19 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,779, price is now $1,640 per person
$1,640
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.2/10 Wonderful! (106 reviews)
So great all around!

Reviewed on Jan 4, 2026

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $2,200, price is now $2,038 per person
$2,038
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Ski slopes were accessible and pool was really nice.

Reviewed on Dec 27, 2025

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Westmoreland Hotel Deals

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$336 nightly
The price is $369 total per night from Feb 2 to Feb 3
$369 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (250 reviews)
Ski slopes were accessible and pool was really nice.

Reviewed on Dec 27, 2025

Mount Snow Grand Summit Resort
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Jan 14 to Jan 15
$93 total
Jan 14 - Jan 15
Total with taxes and fees
7.6/10 Good! (1,004 reviews)
staff was wonderful. the room was clean. hotels dot com said breakfast is included but there was no breakfast included at this hotel. this was important to me as my car broke down and I had no transportation so I was a little upset about that. there was a food market in walking distance and a microwave ...

Reviewed on Jan 10, 2026

The Covered Bridge Inn
Valley Craft Ales

Valley Craft Ales

2 out of 5
18 N Main St Wilmington VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Jan 25 to Jan 26
$149 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (193 reviews)
Clean simple room over the brewery was convenient for dinner and relaxing after. Being right on the main road wasn't loud, but made it a little difficult to get in and out of with traffic, especially with slightly slippery conditions.

Reviewed on Jan 11, 2026

Valley Craft Ales
See all 1,203 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.

Find the Best Westmoreland Vacation Packages

Westmoreland Essential Information

Language
English
Currency
U.S dollars
Population
1,850
Top Sights
Walpole Mountain View Winery, Hooper Golf Club and Walpole Artisans Cooperative

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Frequently asked questions

How much does a Westmoreland vacation package cost?
You'll find cheap prices from $703 on Expedia for your Westmoreland break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Westmoreland costs.
What are the cheapest months to go to Westmoreland?
You're likely to find lower prices and better availability in January, October and December. Explore our cheap Westmoreland vacation packages and you could land some great off-season deals.
How many days is enough for Westmoreland?
The ideal length of your Westmoreland vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to check out all the main attractions and discover some hidden spots along the way.
How to find the best Westmoreland package deals?
Begin your search for a Westmoreland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Westmoreland package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Westmoreland adventure off to a flying start.
Is it cheaper to book a Westmoreland vacation as a package?
You can enjoy significant savings on your Westmoreland break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Westmoreland?
If you have your Westmoreland travel dates finalized, book early to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Westmoreland vacation packages?
Set off on your perfect escape to Westmoreland with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.