Whitingham Vacations from $696

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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.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $779, price is now $696 per person
$696
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
9.2/10 Wonderful! (1,007 reviews)
Super cute and super convenient to skiing. Nice restaurant and heated pool. Friendly staff.

Reviewed on Mar 21, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,064, price is now $874 per person
$874
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
8.8/10 Excellent! (914 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!

Reviewed on Jan 30, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $801, price is now $700 per person
$700
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
The hotel is charming. The location is great. The building is funky, given it's age and need for repair. The staff are friendly, helpful, and knowledgeable. The theater located in the same building is a one of a kind attraction. It was a plus for us that the hotel is owned and run by a nonprofit.

Reviewed on Mar 22, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $861, price is now $762 per person
$762
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $826, price is now $738 per person
$738
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Rutland (RUT)
8.6/10 Excellent! (1,003 reviews)
Really friendly and helpful staff. Excellent bar and grille, pool and exercise room with generous hours. A little noisy as some parents let their kids free range about. However, very comfortable room, beds and great views.

Reviewed on Mar 19, 2026

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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
$691 nightly
The price is $774 total per night from Mar 23 to Mar 24
$774 total
Mar 23 - Mar 24
Total with taxes and fees
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! (47 reviews)
Wonderful property - bedrooms were great and heat worked well for a very cold weekend stay! Great house for a large group - appreciate the large spaces to hang out as a group - from the huge dining room table to the large living room on the third floor. Plenty of space to be together as well as be ...

Reviewed on Jan 3, 2026

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Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.

Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.

Whitingham VT
9.8/10 Exceptional! (11 reviews)
We had a great stay! Everything was easy and communication was clear!

Reviewed on Nov 18, 2025

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Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.
See all 1,371 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 $696 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.