Milton Vacations from $223

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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.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $427, price is now $223 per person
$223
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (1,825 reviews)
Lovely property in midtown with lots of local restaurants - fantastic to be able to walk to Times Sq and attractions

Reviewed on Nov 30, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $627, price is now $287 per person
$287
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
We loved it and the restaurant but for Friday night. We were on the 10th floor and the he music from the Event space on the 12th floor shock and pounded us till 4 am. If you like to sleep at night come here weeknights ONLY!

Reviewed on Nov 29, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $704, price is now $341 per person
$341
per person
Jan 15 - Jan 18
found 10 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $703, price is now $348 per person
$348
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (3,348 reviews)
Room was perfect. Excellent location. Breakfast is worth it.

Reviewed on Dec 1, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $517, price is now $263 per person
$263
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
Cute hotel. Friendly Staff

Reviewed on Dec 1, 2025

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Milton Hotel Deals

Buttermilk Falls Inn

Buttermilk Falls Inn

3 out of 5
220 N Rd Milton NY
$431 nightly
The price is $482 total per night from Dec 4 to Dec 5
$482 total
Dec 4 - Dec 5
Total with taxes and fees
9.4/10 Exceptional! (38 reviews)
The sheets were stained with blood. The bed was completely broken on one side. I was unable to sleep comfortably. We are still waiting to be contacted by someone from the hotel.

Reviewed on Nov 12, 2025

Buttermilk Falls Inn
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
$99 nightly
The price is $115 total per night from Dec 12 to Dec 13
$115 total
Dec 12 - Dec 13
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Comfortable room

Reviewed on Nov 30, 2025

Hampton Inn & Suites Poughkeepsie
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Jan 1 to Jan 2
$114 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (1,016 reviews)
Good hotel. No frills

Reviewed on Nov 29, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
See all 1,118 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 $223 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.