Westmoreland Vacations from $1,081

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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
per person
Oct 21 - Oct 24
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
8.8/10 Excellent! (791 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.

Reviewed on Aug 1, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
per person
Oct 3 - Oct 6
found 13 hours ago
Roundtrip non-stop flight included
Omaha (OMA) to Springfield (VSF)
9.6/10 Exceptional! (54 reviews)
everybody was so kind! we had a wonderful room for such a cheap price, I couldn't resist to choose this inn. The house keeper was so sweet and so was the owner! I will definitely be coming back :)

Reviewed on Jul 29, 2025

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
Oct 21 - Oct 24
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
9.4/10 Exceptional! (27 reviews)
The owner was very attentive and helpful with all of our requests. He was truly thankful for us staying at the Inn. The Inn was nicely decorated and full of history which was shared throughout. The outside area was inviting with different seating options from couches to tables and chairs to Adirondack chairs under a tree and by the river. There was also a 2 seater swing. This is a historical building and we had to walk up about a dozen steps to our room, which may pose a problem for some. We will definitely be staying here again! I would highly recommend Lincoln Inn!

Reviewed on Aug 4, 2025

The Vesper

The Vesper

3 out of 5
per person
Oct 15 - Oct 18
found 17 hours ago
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
9.2/10 Wonderful! (24 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on Jul 17, 2025

Stay At Jimmy's

Stay At Jimmy's

3 out of 5
per person
Oct 21 - Oct 24
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
10/10 Exceptional! (38 reviews)
Everything was amazing!!! We will definately go back.

Reviewed on Jul 21, 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
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $139 total per night from Aug 11 to Aug 12
$139 total
Aug 11 - Aug 12
Total includes taxes and fees
6.6/10 (1,000 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on Jul 28, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Sep 4 to Sep 5
$134 total
Sep 4 - Sep 5
Total includes taxes and fees
8/10 Very Good! (858 reviews)
"this is a very nice hotel, and we have stayed before and will stay again, but we will never stay in 212 again, they play music in the lobby and halls 24/7 which is fine, but 212 is right over the lobby and you can hear the drumming all night, it is very irritating, but like I said we have stayed ..."

Reviewed on Aug 4, 2025

Hampton Inn Brattleboro
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
$125 nightly
The price is $136 total per night from Aug 14 to Aug 15
$136 total
Aug 14 - Aug 15
Total includes taxes and fees
8.4/10 Very Good! (871 reviews)
"Is a very well cared for hotel and I enjoyed my stay and I’ve stayed there several times."

Reviewed on Aug 5, 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 1,121 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 $1,081 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.