
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.

The Vermont Inn
Price was CA $1,744, price is now CA $1,442 per person
CA $1,442
per person
Oct 12 - Oct 18
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.
Reviewed on Jul. 23, 2025

The Shire Woodstock
Price was CA $4,107, price is now CA $2,938 per person
CA $2,938
per person
Oct 12 - Oct 18
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Springfield (VSF)
8.8/10 Excellent! (811 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

Lake Bomoseen Lodge
Price was CA $2,000, price is now CA $1,610 per person
CA $1,610
per person
Oct 12 - Oct 18
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Rutland (RUT)
9.4/10 Exceptional! (814 reviews)
Lovely lakeside view. Unhappy that we were placed (without need or request) in a handicapped-accessible room with a shower that splashed water onto the bathroom floor, soaking it. No seat cover on toilet, huge chair inside shower that we had to move out. We should have been told this when we made the reservation (much earlier than friends of ours in an adjacent non-handicapped room!)
Reviewed on Aug. 27, 2025


Killington Mountain Lodge, Tapestry Collection by Hilton
Price was CA $2,181, price is now CA $1,779 per person
CA $1,779
per person
Oct 12 - Oct 18
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Very friendly staff! Jess the receptionist allowed us to check in at 10am rather than 4pm! The ladies working the bar and strabucks counter were super friendly and helpful. The property manager accommodated myself and kids even though the hot tub was out of service, jets didn’t work and it wasn’t hot, she brought us new towels and allowed us to stay in the pool.
Reviewed on Aug. 26, 2025
Whitingham Hotel Deals

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

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 28 to Sep 29
CA $207
CA $232 total
Sep 28 - Sep 29
includes taxes & fees

The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $282 per night from Sep 7 to Sep 8
CA $282
CA $316 total
Sep 7 - Sep 8
includes taxes & fees
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.