Milton Vacation Packages
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Your Milton Vacation
When a city escape is calling, answer it with a vacation package to Milton. With all your travel plans taken care of before you leave, all you have to do here is concentrate on having a blast. Milton House Museum and Northleaf Winery are some of the top attractions to check out during a trip to Milton. Whoever you're traveling with and whatever you want to spend, your ultimate Milton vacation is just a few clicks away with Expedia.
Top Milton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Bluegreen Odyssey Dells
Lake Delton
Price was CA $1,414, price is now CA $1,158 per person
CA $1,158
per person
Apr 18 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (159 reviews)
The staff at the establishment were very welcoming and accommodating, and Tyler in particular stood out for his friendly and helpful demeanor. He made our experience even more enjoyable and stress-free. We highly recommend this place for their exceptional staff and service.
Reviewed on Jan 11, 2026
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort
Price was CA $1,602, price is now CA $1,210 per person
CA $1,210
per person
Apr 18 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
8.4/10 Very Good! (122 reviews)
didn't ski or use pool but setting was very good and staff friendly. liked upstairs downstairs bedrooms
Reviewed on Dec 27, 2025
The Madison Concourse Hotel and Governor's Club
Downtown Madison
Price was CA $1,623, price is now CA $1,284 per person
CA $1,284
per person
Apr 18 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (3,305 reviews)
Great staff, good size rooms, clean and good location
Reviewed on Feb 1, 2026
Comfort Suites Cottage Grove – Madison
Village of Cottage Grove
Price was CA $1,708, price is now CA $1,368 per person
CA $1,368
per person
Apr 18 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (431 reviews)
The Manager was supportive and friendly. The room was fine.
Reviewed on Jan 17, 2026
Milton Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Feb 15 to Feb 16
CA $134
CA $183 total
Feb 15 - Feb 16
includes taxes & fees
8.4/10 Very Good! (1,726 reviews)
Fun weekend great food great vibes. The staff is always friendly and helpful.
Reviewed on Feb 5, 2026
Lake Lawn Resort
2400 E Geneva St Delavan WI
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Feb 9 to Feb 10
CA $118
CA $175 total
Feb 9 - Feb 10
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Everything was excellent
Reviewed on Feb 2, 2026
Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG
200 W O CONNOR DRIVE Elkhorn WI
Fully refundable
The price is CA $142 per night from Feb 15 to Feb 16
CA $142
CA $159 total
Feb 15 - Feb 16
includes taxes & fees
9.2/10 Wonderful! (698 reviews)
Room was clean and ready for us. The staff were polite and extremely professional.
Reviewed on Feb 3, 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.
