Westmoreland Vacations from $712

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The Latest Westmoreland vacation packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $841, price is now $712 per person
$712
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,357, price is now $1,037 per person
$1,037
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.8/10 Excellent! (917 reviews)
Everything was great.

Reviewed on Apr 8, 2026

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
Price was $880, price is now $721 per person
$721
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (65 reviews)
Super friendly and knowledgeable staff. The Inn is historic, in a lovely spot, and reasonably priced. Dining recommendations were spot on.

Reviewed on Apr 12, 2026

The Vesper

The Vesper

3 out of 5
Price was $980, price is now $812 per person
$812
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
9.2/10 Wonderful! (57 reviews)
Uniqueness of rooms, breakfast options and walking distance to so many great spots!

Reviewed on Feb 18, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $914, price is now $782 per person
$782
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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Westmoreland Hotel Deals

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
6.8/10 (1,002 reviews)
Awesome and clean and quiet love the staff

Reviewed on Apr 14, 2026

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Colonial Motel And Spa
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Apr 16 to Apr 17
$120 total
Apr 16 - Apr 17
Total with taxes and fees
8.8/10 Excellent! (85 reviews)
Beautifully modernized Inn. Well maintained and very clean. The entire check in/out process was smooth, hot tub was easy to use, and the room was impeccable. 100% recommend to anyone. For the skiers/boarders, they even have a whole room with boot dryers, no more resorting to hair dryers!

Reviewed on Apr 13, 2026

Hideaway Inn Mt. Snow
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $157 total per night from Apr 20 to Apr 21
$157 total
Apr 20 - Apr 21
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
See all 1,170 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 $712 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.