Milton Vacations from $690
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Club Wyndham Tamarack
$690
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.4/10 Exceptional! (24 reviews)
The room was spotless and it was nice to relax with the fireplace. Also enjoyed saving money by buying and cooking our own meals.
Reviewed on May 12, 2026
The Madison Concourse Hotel and Governor's Club
Downtown Madison
$784
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.4/10 Exceptional! (4,084 reviews)
I went during Epic UGM week. At over $400 a night, this is a terrible value even for a busy time. Ive stayed at hotels that cost half as much during the same time that are just outside Madison that are just as nice or nicer. If youre paying more than $250 a night for this place, prepare to be disappointed. First and last time staying there.
Reviewed on Aug 19, 2026
Dellshire Resort
$759
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9/10 Wonderful! (270 reviews)
Dellshire Resort is such an amazing place the staff was awesome our room was very nice and big it accommodated all 6 of us perfectly. It offers everything you need if you didn't want to go out. We ate breakfast at the Blade &Barrel it was amazing. This hotel looks like a castle and is so neat inside we will definitely be going back.
Reviewed on Aug 20, 2026
Stay near popular Milton attractions
Milton House Museum
7.4/10 (6 reviews)
This historic hexagonal inn served as a crucial Underground Railroad stop, featuring a preserved escape tunnel. Tour the 1844 stagecoach station and experience candlelit Twilight Tours with historical reenactors.
Northleaf Winery
Housed in a historic 1850s building, Northleaf Winery crafts award-winning small-batch wines. Sample their diverse selection through complimentary tastings while enjoying the restored tasting room's charming ambiance.
Bonny Meade Driving Range
This Scottish links-style 9-hole course recreates the minimalist design and natural terrain of traditional Scottish golf. Enjoy open fairways and classic elements for an authentic links experience.
Milton Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$165 nightly
$183 total
Sep 3 - Sep 4
Total with taxes and fees
8.6/10 Excellent! (2,010 reviews)
"Stayed with my family for weekend getaway and it had everything we needed for adults and kids!"
Reviewed on Aug 20, 2026
Lake Lawn Resort
2400 E Geneva St Delavan WI
Fully refundableReserve now, pay when you stay
$153 nightly
$173 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,014 reviews)
"The property was very nice, and the flowers were very pretty. I liked the rocking chairs outside our room. It would have been helpful to have a fan in the bathroom."
Reviewed on Aug 19, 2026
Baymont by Wyndham Janesville
616 Midland Rd Janesville WI
Fully refundableReserve now, pay when you stay
$69 nightly
$78 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"a"
Reviewed on Aug 19, 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Milton vacation package cost?
Offering great value package deals from $690 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.
Explore a world of travel with Expedia
- Cabin Rentals in Milton
- 4 Star Hotels in Milton
- B&B in Milton
- Motels in Janesville
- Pet-Friendly Hotels in Janesville
- Fort Atkinson Hotels
- Newville Hotels
- Hotels with an Outdoor Pool in Janesville
- Resorts in Milton
- Cabin Rentals in Janesville
- Lake Geneva Hotels
- Delavan Hotels
- Beach Hotels in Milton
- Hotels with Restaurants in Janesville
- Hotels near Glacial River Bike Trail
- Hotels with a Pool in Janesville
- Cabin Rentals in Lake Geneva
- Historic Hotels in Milton
- Hotels with an Outdoor Pool in Milton
- Downtown Madison Hotels
- Hotels with Bars in Janesville
- Best Western Hotels in Janesville
- Luxury Hotels in Janesville
- Whitewater Hotels
- Edgerton Hotels
- Madison Hotels
- Hotels with Hot Tubs in Janesville
- Rv Parks in Milton
- Hotels with an Indoor Pool in Janesville
- Cheap Hotels in Janesville
- 3 Star Hotels in Milton
- Milwaukee Hotels
- Downtown Milwaukee Hotels
- Cheap Hotels in Milwaukee
- Motels in Milton
- Stoughton Hotels
- Janesville Hotels
- Hotels with a Pool in Milton
- Cheap Hotels in Madison
- Milton Hotels
- Romantic Hotels in Janesville
- Flights from Chicago (ORD) to Madison (MSN)
- Flights from Los Angeles (LAX) to Madison (MSN)
- Flights to Milwaukee
- Flights from Dane County Regional
- Flights from Milton
- Flights to Milton
- Flights from Southern Wisconsin Regional
- Flights from Denver (DEN) to Madison (MSN)
- Flights from Boston (BOS) to Madison (MSN)
- Flights from Janesville
- Flights to Edgerton
- Flights to Janesville
- Flights to Madison
- Flights from New York (LGA) to Madison (MSN)
- Flights from Madison
- Lake Ripley Park Beach
- Lake Kegonsa State Park
- Stoughton Vacations
- Drill Hall Theater at the Armory
- Beloit Vacations
- Edgerton Vacations
- Traxler Park
- Panther Intaglio Effigy Mound
- Dancing Goat Distillery
- Troll Beach
- Dancing Horse Theatre
- Korth Park
- Visit Lake Geneva
- Hinchley's Dairy Farm
- Visit Janesville
- Whitewater Vacations
- Fireside Dinner Theatre
- Walworth County Fairgrounds
- Elkhorn Vacations
- Lake Mills Vacations
- Logan Museum of Anthropology
- Aztalan State Park
- Lincoln-Tallman House
- Visit Milton
- Janesville Vacations
- Watsons Wild West Museum
- Milton House Museum
- Allen Creek Gallery
- Edgerton Towne Country Club
- Rotary Botanical Gardens
- Cambridge Winery
- Busy Barns Adventure Farm
- Irvin L.Young Auditorium
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
