Jefferson Vacation Packages
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Your Jefferson Vacation
Take the hassle out of travel planning by booking a Jefferson vacation package. One of the best neighborhoods to stay in this captivating city is Rockdale, which is great for watersports and plenty more. Fill your days with tours of Johnson Creek Premium Outlets, Jefferson County Fairgrounds and Busy Barns Adventure Farm, some of the things you shouldn't miss during your trip to Jefferson. A couple of clicks is all it takes to put together a tailor-made Jefferson vacation on Expedia.
Top Jefferson Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Valued Stay Sun Prairie
Price was CA $1,070, price is now CA $978 per person
CA $978
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Madison (MSN)
7/10 Good! (559 reviews)
The property itself is pretty run down. The parking lot was terrible there's potholes everywhere. The bed was super comfortable. Although my TV didnt work - the wifi doesnt work down at the end of the building. I had to run a channel search just to get antenna channels. The TV is tiny too. There were people standing outside smoking cigarettes and listening to music late into the night, which doesnt really bother me but still something to note.
Reviewed on May 13, 2026
Valued Stay Aloha
Carpenter Ridgeway
Price was CA $1,292, price is now CA $1,149 per person
CA $1,149
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Madison (MSN)
7.6/10 Good! (322 reviews)
Property is clean and looks to be renovated. Staff at checkin was excellant
Reviewed on May 13, 2026
Valued Stay Mayflower
Burr Oaks
Price was CA $1,284, price is now CA $1,153 per person
CA $1,153
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Madison (MSN)
6.4/10 (421 reviews)
Only thing going for it is cheap room. Staff not around, no air, no thermostat in room, no coffee for breakfast, cold ceral is only menu item. You get what you pay for.
Reviewed on Apr 15, 2026
Hotel Ruby Marie
Downtown Madison
Price was CA $1,221, price is now CA $1,100 per person
CA $1,100
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Madison (MSN)
9.4/10 Exceptional! (1,002 reviews)
Just FYI, Room 11 faces the train tracks and the train WILL wake you up in the morning. Best alarm clock ever. I was very delightfully surprised how well maintained the hotel is and how nice the room was.
Reviewed on May 8, 2026
Jefferson Hotel Deals
Best Western Plus Jefferson
1409 W JUNCTION ROAD Jefferson WI
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from May 26 to May 27
CA $136
CA $150 total
May 26 - May 27
includes taxes & fees
9.6/10 Exceptional! (378 reviews)
yes
Reviewed on May 14, 2026
AmericInn by Wyndham Jefferson
1456 S Ryan Ave Jefferson WI
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from May 21 to May 22
CA $105
CA $116 total
May 21 - May 22
includes taxes & fees
8.2/10 Very Good! (476 reviews)
Our room was not clean, the tub faucet wasnt attached to the wall, one wall had a large dent, the bedspread had stains, the free lotion had been open and used, but worse of all, the exit door closest to our room was broken and you could get in, but not out! Fire trap?? The desk clerk said it was ...
Reviewed on May 10, 2026
Holiday Inn Express & Suites Delafield by IHG
3030 Golf Rd Delafield WI
Fully refundable
The price is CA $144 per night from May 25 to May 26
CA $144
CA $163 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (644 reviews)
Great hotel! Very clean, good coffee in the lobby, friendly staff
Reviewed on May 10, 2026
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.
