Westmoreland Vacations from $313

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The Latest Westmoreland vacation packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $377, price is now $313 per person
$313
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.4/10 Very Good! (789 reviews)
Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful.

Reviewed on Sep 28, 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $781, price is now $601 per person
$601
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (VSF)
7.8/10 Good! (1,003 reviews)
Clean, comfortable room. Modest continental breakfast.

Reviewed on Sep 26, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $434, price is now $352 per person
$352
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
8.8/10 Excellent! (507 reviews)
The property was well kept and was close to different trails and beautiful views. We felt safe and comfortable. We want to come back in the winter to stay again!

Reviewed on Sep 30, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $658, price is now $557 per person
$557
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (VSF)
8.8/10 Excellent! (223 reviews)
Great place to stay!

Reviewed on Sep 25, 2025

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $462, price is now $411 per person
$411
per person
Nov 14 - Nov 16
found 20 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
9.8/10 Exceptional! (90 reviews)
The perfect stay! A lot of hard work goes into the experience here. It's evident in everything from the furnishings to the gardens, paint work, carpets, bedding, amenities, and yes the food was excellence. The breakfast was hand made home cooked perfection. For anyone looking for a perfect hostess and private, quiet stay it's amazing. Thankyou for all of the work that goes into providing this. We stayed in a luxury hotel in quebec a few days back and the price was a lot more and the experience incomparable. Your Inn is far better. Thankyou!

Reviewed on Aug 5, 2025

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Westmoreland Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Oct 26 to Oct 27
$136 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (908 reviews)
"Very clean, up to date, affordable"

Reviewed on Sep 29, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $125 total per night from Oct 6 to Oct 7
$125 total
Oct 6 - Oct 7
Total with taxes and fees
8.6/10 Excellent! (514 reviews)
"There was no staff on duty and the carpet in the room was not vacuumed and there was no ice machine"

Reviewed on Sep 23, 2025

Mountaineer Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
$140 nightly
The price is $154 total per night from Oct 31 to Nov 1
$154 total
Oct 31 - Nov 1
Total with taxes and fees
8.2/10 Very Good! (889 reviews)
"The hotel was clean and organized but I found the HVAC unit full of black mold. The bed made my back hurt."

Reviewed on Sep 20, 2025

Hampton Inn Brattleboro
See all 1,143 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 $313 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.