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.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,502, price is now CA $1,264 per person
CA $1,264
per person
Sep 9 - Sep 14
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Property beautiful.
Rooms very large.
Staff very friendly.
The only thing that was odd to me was none of our closets had rods to hang clothes on. We were going to a formal wedding, my husband had a suit and I had a long dress to hang up, but the closets had no rods, and we had 3 closets in our room.
Had to hang the suit from a door handle and the long dress from the shower rod!
Reviewed on Jun 28, 2026
The Shire Woodstock
Price was CA $2,698, price is now CA $2,097 per person
CA $2,097
per person
Sep 9 - Sep 14
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (935 reviews)
Facilities were nice & clean. Office staff were very friendly & helpful! Rooms were large and very nice & clean! Beautiful views of the Ottauquechee River. Fun grassy area with fire pits & cornhole along the edge of the river. Walking distance to the downtown area with shops & restaurants!
Reviewed on Jun 30, 2026
The Vesper
Price was CA $2,023, price is now CA $1,690 per person
CA $1,690
per person
Sep 9 - Sep 14
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
9.2/10 Wonderful! (63 reviews)
Absolute gem on the edge of.downtown. super walkable everywhere in terms of shopping, and within a 5 min drive to less pricier food options away from downtown. Jessica was an amazing and gracious host. The oatmeal with maple syrup, apples and walnuts was the quintessential Vermont start to the day. So many unique touches in terms of aesthetics made it feel homey yet held to the character of a nearly 200 year old home. Stay here.
Reviewed on Jun 25, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,902, price is now CA $1,591 per person
CA $1,591
per person
Sep 9 - Sep 14
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Whitingham Hotel Deals
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham VT
The price is CA $687 per night from Jul 15 to Jul 16
CA $687
CA $1,153 total
Jul 15 - Jul 16
includes taxes & fees
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."
Reviewed on May 25, 2026
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Whitingham VT
9.8/10 Exceptional! (50 reviews)
"The Sawyer Mansion was perfect for our family of 13. Plenty of room for everyone to have their own space plus areas for the whole family to gather. The house was clean and the kitchen was filled with more than enough dishes, pots, pans, silverware etc. for large gatherings. Our family also enjoyed ..."
Reviewed on Jun 1, 2026
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Whitingham VT
10/10 Exceptional! (50 reviews)
"We had 3 lovely nights at the Lakeside Tiny House and spent some wonderful time hiking in nearby state parks. The view of the lake is perfection and the house was just right for my husband and I. Highly recommend."
Reviewed on Sep 7, 2025
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.
