Milton Vacations from $427

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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.

The Latest Milton vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

2.5 out of 5
Price was $493, price is now $427 per person
$427
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
9.2/10 Wonderful! (102 reviews)
Pool was great. The Manager was the Best, she was very empathetic whilevwe going through the worst trauma - my 35 year old hasvLate Stage Progressive Pulmonary Fibrosis with only 1-2 years to live unless she gets a double lung transplant, daughter going through extremely rigorous, long, exhausting evaluations, tests, meetings, to see if she can even get on the Stephanie Gerndt’s Help Hope Live Campaign Page is live! {https://helphopelive.org/campaign/26376/} YOU CAN Help Save Her Life with our GREATEST OF GREAT GRATITUDES! Please Donate, can be bits at a time over time. Spread word to your Churches, other Organizations, Families, Friebfs, etc. I will have Fliers and Business Carfs as well to distribute. Feel free to post messages to Dear Stephie on here as well.

Reviewed on Nov 21, 2025

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $581, price is now $476 per person
$476
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
9.2/10 Wonderful! (1,003 reviews)
Beautiful hotel in a fabulous location

Reviewed on Nov 19, 2025

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $550, price is now $452 per person
$452
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
9/10 Wonderful! (524 reviews)
Great location along the lake and trails

Reviewed on Aug 10, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $535, price is now $442 per person
$442
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
8.6/10 Excellent! (1,004 reviews)
Honestly probably one of the best hotels we’ve stayed at in Madison. Great location, beautiful views of the lake and downtown, easy parking, very clean and updated. Hotel shuttle to Camp Randall was a bonus. Would definitely stay here again and highly recommend.

Reviewed on Nov 24, 2025

Moxy Madison Downtown

Moxy Madison Downtown

3.5 out of 5
Tenney-Lapham
Price was $490, price is now $428 per person
$428
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
9.2/10 Wonderful! (346 reviews)
Very close to the Slyvee which is what we needed.

Reviewed on Nov 22, 2025

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Discover the most popular places to visit in Milton

Milton House Museum

You can learn about the history of Milton with a trip to Milton House Museum. While in this family-friendly area, you can savor the top-notch restaurants.

Milton House Museum

Northleaf Winery

You can enjoy a tasting or tour at Northleaf Winery during your travels to Milton. Stroll along the riverfront or attend a sporting event in this family-friendly area.

Northleaf Winery

Milton Hotel Deals

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $125 total per night from Nov 30 to Dec 1
$125 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (1,665 reviews)
All staff were great and kind to us except one. Austin at the waterfront bar. He was rude, expected us to know what we wanted to order the second we sat down. Rolled his eyes, processed to ignore us and served/check on other customers. When we asked him to break a $20 he again rolled his eyes. The ...

Reviewed on Nov 23, 2025

Abbey Resort and Avani Spa
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $151 total per night from Nov 30 to Dec 1
$151 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
This was a Mom and Son getaway for the weekend. Very much needed! We had so much just relaxing and talking, enjoying the quiet time, using the pool. He's a teenager and met some other teens and had a blast! It was really good for him. Very much needed for a little sibling separation. And I've been ...

Reviewed on Nov 16, 2025

Lake Lawn Resort
Motel 6 Janesville, WI

Motel 6 Janesville, WI

2 out of 5
3907 Milton Ave Janesville WI
Fully refundableReserve now, pay when you stay
$47 nightly
The price is $53 total per night from Nov 29 to Nov 30
$53 total
Nov 29 - Nov 30
Total with taxes and fees
6.8/10 (829 reviews)
Great rooms workers and front desk people are great property looks great

Reviewed on Nov 20, 2025

Motel 6 Janesville, WI
See all 443 properties in Milton
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.

Find the Best Milton Vacation Packages

Milton Essential Information

Language
English
Currency
U.S dollars
Population
5,600
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Northleaf Winery and Milton House Museum

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Frequently asked questions

How much does a Milton vacation package cost?
Offering great value package deals from $427 on Expedia, you'll be thrilled with how little a vacation to Milton costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Milton?
If you'd like to snag a cheap Milton vacation package, consider planning a trip in December, January and February. You'll usually find better rates on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Milton?
The ideal duration for your Milton vacation depends on what you'd like to see. Typically, a few days to a week will give you enough time to visit all the top sights and discover some hidden gems along the way.
How to find the best Milton package deals?
Start your search for a Milton package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Milton package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Milton escape underway.
Is it cheaper to book a Milton vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Milton vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Milton?
If you're planning a spontaneous Milton vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Milton vacation packages?
Your Milton getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.