Milton Vacations from $316
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Your Milton Vacation
The welcoming locals and rich traditions are just the beginning of the things Milton has going for it. Experience the best of this interesting city your way with a personalized Milton vacation package. Benmarl Vineyards and Winery, Live At The falcon and Gomez Mill House are just a few of the many sights you'll want to check out during your trip to Milton. A couple of quick clicks is all it takes to build your perfect Milton vacation on Expedia.
The Latest Milton vacation packages
Price found within the past 48 hours. Click for updated prices.
Milton Hotel Deals
Buttermilk Falls Inn
220 N Rd Milton NY
$494 nightly
$553 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (72 reviews)
"Beautiful location and charming inn. Comfy bed. Could have been cleaner in the bathroom. This place could be amazing if it was maintained. Views of the Hudson River were covered by the messy gardens and trees. No restaurant."
Reviewed on Oct 12, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
$109 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (1,124 reviews)
"Clean rooms, really helpfull Staff breakfast was amazing."
Reviewed on Oct 16, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$169 nightly
$191 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
"I booked this stay over the NY Sheep and Wool festival weekend. I was confused when the receptionist started giving me directions to a building outside. The whole point was to stay in the historic hotel- not a bungalow outside. Anyway, we were there overnight. Dinner in the tavern was definitely ..."
Reviewed on Oct 18, 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 |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 1,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Robibero Winery, Benmarl Vineyards and Winery and Adair Vineyards |
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Frequently asked questions
How much does a Milton vacation package cost?
Offering excellent value package deals from $316 on Expedia, you'll be pleasantly surprised at how much a vacation to Milton costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Milton?
If you're looking to score a cheap Milton vacation package, consider traveling in November, December and January. You're likely to find lower prices on flights and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Milton?
Typically, a handful of days is enough to go to the top attractions during your Milton vacation. However, if you want to have more time to kick back or go on day trips, consider extending your trip.
How to find the best Milton package deals?
Start your search for a Milton package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Milton package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Milton getaway off to a flying start.
Is it cheaper to book a Milton vacation as a package?
You can enjoy significant savings on your Milton escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Milton?
If you're considering a spontaneous Milton adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Milton vacation packages?
Jet off on your perfect escape to Milton with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up bargains before they sell out.
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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.
