Westmoreland Vacations from $494

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The Latest Westmoreland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $661, price is now $494 per person
$494
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
Easy check in and good parking

Reviewed on Jan 9, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $928, price is now $724 per person
$724
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
This place is a must stay, I’ll come back every year. So Beautiful.

Reviewed on Jan 9, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $739, price is now $597 per person
$597
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.4/10 Very Good! (822 reviews)
Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!

Reviewed on Dec 31, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,653, price is now $1,354 per person
$1,354
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Save 100% on your flight
Price was $2,189, price is now $1,795 per person
$1,795
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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! (249 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
$74 nightly
The price is $81 total per night from Jan 11 to Jan 12
$81 total
Jan 11 - Jan 12
Total with taxes and fees
7.6/10 Good! (1,003 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 2025

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
$138 nightly
The price is $151 total per night from Jan 14 to Jan 15
$151 total
Jan 14 - Jan 15
Total with taxes and fees
8.4/10 Very Good! (192 reviews)
Friendly staff, value for money

Reviewed on Jan 1, 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 $494 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.