Whitingham Vacations from $291

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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 Vermont Inn

The Vermont Inn

3 out of 5
Price was $366, price is now $291 per person
$291
per person
Oct 31 - Nov 2
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.2/10 Wonderful! (408 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $495, price is now $363 per person
$363
per person
Oct 31 - Nov 2
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.8/10 Excellent! (823 reviews)
Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river.

Reviewed on Sep 25, 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $775, price is now $621 per person
$621
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
7.8/10 Good! (1,003 reviews)
Clean, comfortable room. Modest continental breakfast.

Reviewed on Sep 26, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $662, price is now $574 per person
$574
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $629, price is now $548 per person
$548
per person
Oct 31 - Nov 3
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
9.8/10 Exceptional! (90 reviews)
The perfect stay! A lot of hard work goes into the experience here. It's evident in everything from the furnishings to the gardens, paint work, carpets, bedding, amenities, and yes the food was excellence. The breakfast was hand made home cooked perfection. For anyone looking for a perfect hostess and private, quiet stay it's amazing. Thankyou for all of the work that goes into providing this. We stayed in a luxury hotel in quebec a few days back and the price was a lot more and the experience incomparable. Your Inn is far better. Thankyou!

Reviewed on Aug 5, 2025

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Whitingham Hotel Deals

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
9.6/10 Exceptional! (46 reviews)
"It was good but a little disappointing in the lake. Entry to the lake was not good for the eight-year-old and the 11-year-old . I guess I didn’t realize that when I booked it the house was great. The area was great."

Reviewed on Aug 13, 2025

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Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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
9.6/10 Exceptional! (8 reviews)
"My group had a wonderful time at Black Bear Brook!"

Reviewed on Sep 22, 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!
See all 1,290 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 $291 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.