Whitingham Vacations from $618

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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
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (403 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
per person
Oct 16 - Oct 19
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (791 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.

Reviewed on Aug 1, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
7.2/10 Good! (1,001 reviews)
Views were spectacular

Reviewed on Jul 16, 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
10/10 Exceptional! (7 reviews)
The property was conveniently located near Mt. Sniw.

Reviewed on Jul 26, 2025

The Vesper

The Vesper

3 out of 5
per person
Oct 16 - Oct 19
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
9.2/10 Wonderful! (24 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on Jul 17, 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)
Weekend Get A Way
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's ..."

Reviewed on Oct 15, 2024

Get rates
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $160 total per night from Sep 1 to Sep 2
$160 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Staff was fine- they were fine but didn’t really go the extra mile."

Reviewed on Jul 30, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $259 total per night from Aug 11 to Aug 12
$259 total
Aug 11 - Aug 12
Total includes taxes and fees
9.6/10 Exceptional! (478 reviews)
"The property was spacious but still had a cozy feel."

Reviewed on Jul 29, 2025

The Williams Inn
See all 1,261 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 $618 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.