Whitingham Vacations from $500

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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

Latchis Hotel

2.5 out of 5
Price was $636, price is now $500 per person
$500
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (936 reviews)

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $714, price is now $559 per person
$559
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
10/10 Exceptional! (210 reviews)

The Landgrove

The Landgrove

3.5 out of 5
Price was $1,138, price is now $900 per person
$900
per person
Oct 17 - Oct 21
found 20 hours ago
Roundtrip flight included
Orlando (ORL) to Rutland (RUT)
10/10 Exceptional! (1 review)
Very cool place to stay to get a true feeling of Vermont. Must stay!

Reviewed on Jul 25, 2026

Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $752, price is now $612 per person
$612
per person
Sep 17 - Sep 20
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
10/10 Exceptional! (45 reviews)
Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!

Reviewed on Jul 6, 2026

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,068, price is now $881 per person
$881
per person
Oct 17 - Oct 21
found 20 hours ago
Roundtrip flight included
Orlando (ORL) to Springfield (VSF)
9.2/10 Wonderful! (120 reviews)

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Whitingham Hotel Deals

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
$762 nightly
The price is $853 total per night from Aug 19 to Aug 20
$853 total
Aug 19 - Aug 20
Total with taxes and fees
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on May 25, 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
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! (50 reviews)
"The Sawyer Mansion was perfect for our family of 13. Plenty of room for everyone to have their own space plus areas for the whole family to gather. The house was clean and the kitchen was filled with more than enough dishes, pots, pans, silverware etc. for large gatherings. Our family also enjoyed ..."

Reviewed on Jun 1, 2026

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Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

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

Whitingham VT
10/10 Exceptional! (51 reviews)
"Peaceful, quiet location and aspects of the listing were accurate (nice, green space leading down to the pond). Bedding and towels were nice and clean. Other descriptions were not accurate, or felt overly generous. The listing and welcome email made a big deal about the free breakfast and lunch, ..."

Reviewed on Jul 1, 2026

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Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing
See all 1,354 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 $500 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.