Whitingham Vacations from $562
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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.
Latchis Hotel
$562
per person
Dec 31 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Springfield (VSF)
8.6/10 Excellent! (992 reviews)
It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay.
Reviewed on Oct 21, 2026
Mountain Green Resort
$2,156
per person
Dec 31 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Vikings Villages Resort
$698
per person
Dec 31 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Springfield (VSF)
10/10 Exceptional! (240 reviews)
This is a unique property. Perfect for getting away. Quite, very little to do on the property which is perfect for a truely relaxing get away. Kitchen is set up for cooking your own meals. There is no food available on the premises but a great breakfast spot close by and Brattleboro is also an easy drive away.
Reviewed on Oct 23, 2026
Golden Stage Inn B&B
$1,482
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
10/10 Exceptional! (48 reviews)
Just love this place. Stayed twice. Julie and Mike are such lovely hosts. So down to earth and make you so welcome. Lots of wee special touches and a lovely varied breakfast. Lots of fantastic travel advice too.
Reviewed on Oct 20, 2026
Whitingham Hotel Deals
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
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
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Whitingham VT
10/10 Exceptional! (103 reviews)
"This was our second stay at The Place to Be. We returned because of the beauty of the location and surrounding area and because we had such a positive experience last year. The standard has upheld by the host. The house is clean and has everything one would need! The host is communicative and accommodating. ..."
Reviewed on Oct 12, 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 Whitingham Vacation Packages
Whitingham Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Molly Stark State Park, The Ledge and Lake Raponda |
More vacations you might like
Frequently asked questions
How much does a Whitingham vacation package cost?
You'll find cheap prices from $562 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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- Visit Jacksonville
- Epsilon Spires
- Visit Whitingham
- Prospect Mountain Nordic Ski Center
- Bluebird Express Ski Lift
- Prospect Mountain Cross-Country Ski Center
- Canyon Express Ski Lift
- Hooker-Dunham Theater & Gallery
- The Hermitage Golf Club
- Mount Snow
- Visit Readsboro
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- Visit West Halifax
- The Stone Church
- Grand Summit Express Ski Lift
- Snow Lake
- Heavy Metal Ski Lift
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- Brattleboro Country Club
- Molly Stark State Park
- Visit West Dover
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- Norman Rockwell Exhibition
- Bennington Battle Monument
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- Mount Snow Golf Course
- Southern Vermont Natural History Museum
- Visit Wilmington
- Brattleboro Common
- Stratton Mountain Resort
- Harriman Reservoir
- Guilford Welcome Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
