Westmoreland Vacations from $792
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The Latest Westmoreland vacation packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
$792
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
We had a wonderful stay at the Sinclair Inn Bed & Breakfast in Jericho, Vermont! The house is absolutely beautiful—a charming Queen Anne Victorian filled with character and historic charm. We stayed in Room 5 upstairs, which featured a comfortable king bed and a private bathroom. It was a lovely, comfortable place to relax and enjoy our visit.
Kyle, Holly, and their daughter Cassidy were amazing hosts! They went above and beyond to make us feel welcome. Earlier in our trip, before arriving at the Sinclair Inn, I had injured myself and was on crutches. When we arrived, Kyle graciously helped my wife carry our suitcases upstairs to our room. That thoughtful gesture meant so much to us and really showed the kindness and genuine hospitality of this wonderful family.
Breakfast was delicious, and one of the things we especially enjoyed was the opportunity to sit down, meet, and talk with the other guests. Those conversations added a personal touch to our stay and made the experience even more enjoyable.
Between the beautiful Victorian home, the comfortable accommodations, the delicious breakfast, and the outstanding hospitality, our stay was truly memorable. We highly recommend the Sinclair Inn to anyone visiting Vermont. If you're looking for a beautiful bed and breakfast with wonderful hosts who genuinely care about their guests, this is the place! We would absolutely love to stay here again.
Reviewed on Oct 18, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$1,676
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
8.6/10 Excellent! (908 reviews)
We love this hotel and the views were Amazing.. We stay at Adam’s building and we love to spend relaxing time in the outside jacuzzis , The hotel has a nice indoor restaurant where you can order breakfast. The staff were kind and helpful. We got a suite with one room and we had everything we need to be comfortable with our two kids.
Reviewed on Oct 18, 2026
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Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$164 nightly
$179 total
Nov 18 - Nov 19
Total with taxes and fees
8.6/10 Excellent! (323 reviews)
"Hot tub wasn’t up and running, was looking forward to utilizing that amenity. Food was basically just freezer food, even the salads were below average. Service was great though."
Reviewed on Oct 17, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$99 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
6.2/10 (98 reviews)
"Room wasn’t the cleanest but can tell they’re in the process of renovating. Pet friendly which was amazing and a reasonable price"
Reviewed on Oct 18, 2026
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$97 nightly
$107 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (146 reviews)
"The building is old, small room, not that clean. Outside view is good."
Reviewed on Oct 17, 2026
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 $792 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.