Milton Vacations from $629

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $1,263, price is now $629 per person
$629
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (5,413 reviews)
The lines to check in, check bags, and use the "daily food and beverage credit" were excessive. I'm not sure if this was residual NYE traffic or what, but this was a frustrating delay.

Reviewed on Feb 26, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $2,437, price is now $1,118 per person
$1,118
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,790 reviews)
Room was great. Buffet breakfast was amazing with so many options. Love the fact that a bar and coffee shop are downstairs next to the lobby.

Reviewed on Feb 24, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $2,299, price is now $1,058 per person
$1,058
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
The room size was excellent and very clean. The breakfast each day was great and well organised. Perfect location as Times Square is just around the corner. Would definitely stay here again.

Reviewed on Feb 25, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $2,083, price is now $1,078 per person
$1,078
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,411 reviews)
I stayed here for 4 days with my girlfriend. The hotel is in a great spot with good food spots and cafes within walking distance. Staff are very attentive and helpful. The room is cozy and the shower is probably the best I've seen in a hotel or airbnb. Would 100% recommend

Reviewed on Feb 21, 2026

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Milton Hotel Deals

Buttermilk Falls Inn

Buttermilk Falls Inn

3 out of 5
220 N Rd Milton NY
$494 nightly
The price is $553 total per night from Mar 1 to Mar 2
$553 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (42 reviews)
Management was rude and unprofessional. There were issues with my room (running toilet, broken fireplace) and no attempt was made to rectify the issue. What is advertised on the website is not what the actual experience will be. The worst part was the inability to contact someone in charge because ...

Reviewed on Feb 17, 2026

Buttermilk Falls Inn
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $119 total per night from Mar 15 to Mar 16
$119 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Easy check-in/out. Staff very personable. Clean.

Reviewed on Feb 23, 2026

Courtyard by Marriott Poughkeepsie
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Mar 14 to Mar 15
$109 total
Mar 14 - Mar 15
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
All overall good experience. Thank you,

Reviewed on Feb 26, 2026

Hampton Inn & Suites Poughkeepsie
See all 1,115 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
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 $629 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.