Whitingham Vacations from $958

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Your Whitingham Vacation

Uncover the best of Whitingham with a customized Whitingham vacation package. From its rural countryside and rich history to its spectacular views, you'll love discovering this picturesque city in your own way. Make your trip to Whitingham even more fun and exciting by going sightseeing. Jacksonville Pond, The Ledge and Honora Winery are among the most popular attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Whitingham to suit your travel style, whatever that may be.

The Latest Whitingham vacation packages

Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,181, price is now $958 per person
$958
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
10/10 Exceptional! (250 reviews)

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $1,535, price is now $1,202 per person
$1,202
per person
Dec 24 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
8.8/10 Excellent! (111 reviews)
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!

Reviewed on Nov 8, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,563, price is now $1,254 per person
$1,254
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
No reviews

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,511, price is now $2,075 per person
$2,075
per person
Dec 24 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,754, price is now $1,528 per person
$1,528
per person
Dec 24 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)
Property was in a good location. Very pretty. No tissues in bathroom. Tv did not work. The whole time we were there it had “No service” it read on screen. That wouldn’t have been an issue because I also had an iPad and iphone but the WiFi was sketchy at best.

Reviewed on Nov 13, 2026

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Whitingham Hotel Deals

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham VT
9.8/10 Exceptional! (52 reviews)
"Large unique home that worked perfect for our group of 11 siblings attending our nephews wedding nearby. Wonderful to have so much communal space."

Reviewed on Sep 20, 2026

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Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Whitingham VT
10/10 Exceptional! (104 reviews)
"Wonderful location and great cabin!"

Reviewed on Nov 2, 2026

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Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

Whitingham VT
9.8/10 Exceptional! (57 reviews)
"This Tiny Home was for the most part as described. We expected to be able to use the kayaks, but they were very dirty. The hot tub cover did not fully open, only opened half way. Property description stated breakfast and lunch are included with the price to stay...this was not the case. We didnt ..."

Reviewed on Sep 6, 2026

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Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing
See all 1,334 properties in Whitingham
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 Whitingham Vacation Packages

Whitingham Essential Information

Language
English
Currency
U.S dollars
Top Sights
Molly Stark State Park, The Ledge and Lake Raponda

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Frequently asked questions

How much does a Whitingham vacation package cost?
You'll find cheap prices from $958 on Expedia for your Whitingham break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Whitingham costs.
What are the cheapest months to go to Whitingham?
March, April and October are great times to search for cheap Whitingham vacation packages. Choosing to travel in quieter periods means you can usually find lower prices on flights and accommodations.
How many days is enough for Whitingham?
The ideal duration of your Whitingham vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to check out all the main sights and discover some hidden gems along the way.
How to find the best Whitingham package deals?
Use Expedia's filters to find some unbeatable Whitingham package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Whitingham package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Whitingham vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Whitingham escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Whitingham?
Land fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Whitingham vacation.
Does Expedia offer Book Now, Pay Later Whitingham vacation packages?
Secure your ideal getaway to Whitingham with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split 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 before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.