Whitingham Vacations from $556

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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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $651, price is now $556 per person
$556
per person
Nov 1 - Nov 5
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.4/10 Exceptional! (819 reviews)
Beautiful property right on the lake. We took advantage of the complimentary kayaks which was lovely. The restaurant has beautiful outdoor seating and food and service were excellent. The only negative is that we couldn’t take advantage of the fire pit or lakefront Adirondack chairs because a wedding was taking place.

Reviewed on Sep 10, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $817, price is now $652 per person
$652
per person
Nov 1 - Nov 5
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (815 reviews)
Convenient! Parked the car and didn’t need to get in the car until we left!

Reviewed on Sep 11, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $667, price is now $574 per person
$574
per person
Nov 1 - Nov 5
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Sheets were stained staff was slow and food took way to long. 45 minutes for a grilled cheeze

Reviewed on Sep 14, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,229, price is now $1,072 per person
$1,072
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
The parking lot was larger stones and not easy for rolling suitcases - should check into getting it paved. The mattresses were terrible. Pleasantly surprised by the heated outdoor pool and thoroughly enjoyed it.

Reviewed on Sep 18, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,356, price is now $1,184 per person
$1,184
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (755 reviews)
The hotel was peaceful and clean, perfect for the weekend getaway.

Reviewed on Sep 15, 2025

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Whitingham Hotel Deals

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Whitingham
9.4/10 Exceptional! (7 reviews)
Perfect for a retreat!
"The home was charming and beautiful. The location had beautiful outdoor area that was tranquil. Great surroundings as well. It was the perfect place for our retreat. We will definitely be back again:)"

Reviewed on Jul 21, 2025

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Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
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
10/10 Exceptional! (83 reviews)
"We truly enjoyed our stay at the Place to BE - cozy, quiet & peaceful yet close enough to town if needed. We also appreciate a pet friendly getaway and our pups loved it too! Diane is very responsive & provided lots of helpful information. Thanks so much!"

Reviewed on Sep 10, 2025

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Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $168 total per night from Oct 19 to Oct 20
$168 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)

Reviewed on Sep 15, 2025

Hotel Downstreet, an Ascend Collection Hotel
See all 1,272 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.

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Frequently asked questions

How much does a Whitingham vacation package cost?
You'll find cheap prices from $556 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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