Whitingham Vacation Packages

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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.

Top Whitingham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $1,381, price is now CA $1,221 per person
CA $1,221
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on Aug. 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $3,248, price is now CA $2,507 per person
CA $2,507
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (806 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was CA $2,911, price is now CA $2,356 per person
CA $2,356
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.6/10 Exceptional! (57 reviews)
Very authentic and comfortable.

Reviewed on Aug. 22, 2025

Chalet 239

Chalet 239

2 out of 5
Price was CA $1,600, price is now CA $1,384 per person
CA $1,384
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (74 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept. The free breakfast was a plus.

Reviewed on Aug. 12, 2025

Harvest Barn Inn

Harvest Barn Inn

3 out of 5
Price was CA $1,487, price is now CA $1,317 per person
CA $1,317
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Rutland (RUT)
9.8/10 Exceptional! (223 reviews)
A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again.

Reviewed on Jul. 30, 2025

Ready to book your vacation to Whitingham?

 

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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

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
The price is CA $208 per night from Sep 28 to Sep 29
CA $208
CA $232 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Staff was very helpful and pleasant"

Reviewed on Aug. 24, 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
The price is CA $283 per night from Sep 7 to Sep 8
CA $283
CA $317 total
Sep 7 - Sep 8
includes taxes & fees
The Williams Inn
See all 1,242 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?
Offering great value package deals from CA $1,221 on Expedia, you'll be pleasantly surprised at how much a vacation to Whitingham costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Whitingham?
The off-season is the best time to visit Whitingham if you're hoping to keep costs down. Another tip for finding cheap Whitingham vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Whitingham?
The ideal length of your Whitingham vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to tick off all the top sights and explore some hidden gems along the way.
How to find the best Whitingham package deals?
Begin your search for a Whitingham package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Whitingham package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Whitingham adventure off to a flying start.
Is it cheaper to book a Whitingham vacation as a package?
You can enjoy significant savings on your Whitingham getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Whitingham?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Whitingham adventure.
How to plan a trip to Whitingham?

  1. Choose your dates: The things you'd like to do in Whitingham and your preferred season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your hotel will probably be the biggest expense during your trip to Whitingham.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you want to experience in Whitingham. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Whitingham vacation package.

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