
Whitingham Vacations from $843
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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.




Mountain Green Resort
Price was $1,747, price is now $1,457 per person
$1,457
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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

Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was $2,312, price is now $1,949 per person
$1,949
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Springfield (VSF)
7.6/10 Good! (31 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.
Reviewed on Oct 15, 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

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

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
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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- 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
- Bennington Arts Guild Gallery
- Visit West Halifax
- The Stone Church
- Grand Summit Express Ski Lift
- Snow Lake
- Heavy Metal Ski Lift
- Jim McGrath Gallery and Studio
- Marlboro Vacations
- Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
- Brattleboro Country Club
- Molly Stark State Park
- Visit West Dover
- West Dover Vacations
- Norman Rockwell Exhibition
- Bennington Battle Monument
- Brattleboro Vacations
- 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.


















