Milton Vacations from $481

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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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $842, price is now $481 per person
$481
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,026 reviews)
The location was great especially that we were in the Vity to see a broadway show. The room didn’t have any decorations at all, not one painting. The bed didn’t have a comforter , just sheets and a duvet. The shower faucet was an “ old school” three handle that leaked when used.

Reviewed on Mar 19, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,340, price is now $765 per person
$765
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,782 reviews)
1. Beds squeak so bad - if you breathe the bed squeaks. 2. 5am - the trash truck or whomever start honking their horns ~ ALL MORNING LONG. There is no reprieve from this. 3. No WiFi 4. No laundry/washer available 5. We were never really sure when our room was going to be serviced. 75% it was, but yea… 6. Thin bathtowels 7 The TV has this weird subtitle thing that describes everything happening on the show your watching; there is no shutting this off. Not even worth watching. 8. The shower water is SO HOT it will burn ur skin. Please leave it on minimum for a barely acceptable shower. 9. Mattresses are very… broken in. 10. The convenience of the location was great but for the price, I probably could have went somewhere better. Lesson learned.

Reviewed on Mar 18, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,381, price is now $802 per person
$802
per person
May 6 - May 9
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (143 reviews)
Everything and everyone was just lovely! Comfortable Welcoming Great restaurant

Reviewed on Feb 22, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $883, price is now $567 per person
$567
per person
May 12 - May 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,011 reviews)
Such a charming hotel with wonderful rooms. The Resturant and food are fabulous!

Reviewed on Mar 18, 2026

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $865, price is now $557 per person
$557
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (7,139 reviews)
Needs improvement on property. Missing elevator pad. Our room chair looked like from garage sale (Torn). Lights by bed 1 worked for light but could not plug in phone or devices to charge. Other lamp didn't work at all. Rug on our floor to elevator had tape holding rug down. Should have some kind of map of hotel. Not what I expected for a Sheraton.

Reviewed on Mar 18, 2026

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Milton Hotel Deals

Buttermilk Falls Inn

Buttermilk Falls Inn

3 out of 5
220 N Rd Milton NY
$527 nightly
The price is $590 total per night from Mar 20 to Mar 21
$590 total
Mar 20 - Mar 21
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
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Mar 26 to Mar 27
$107 total
Mar 26 - Mar 27
Total with taxes and fees
7.6/10 Good! (1,009 reviews)
Pool was closed and no table pool sticks

Reviewed on Mar 17, 2026

Best Western Plus Kingston Hotel And Conference Center
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
$102 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
It was a nice stay, no complaints. We will definitely stay here again next time we are in the area!

Reviewed on Mar 17, 2026

Hampton Inn & Suites Poughkeepsie
See all 1,125 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 $481 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.