Milton Vacations from $282

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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.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $484, price is now $282 per person
$282
per person
Apr 7 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
7.8/10 Good! (80 reviews)
The rooms need more amenities such as a coffee maker some cups and utensils, as well as a guide to the television set.

Reviewed on Dec 28, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $861, price is now $461 per person
$461
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The compressor from the heat pump in the room was so loud it would wake me up every time it kicked on all night long

Reviewed on Jan 17, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,894, price is now $1,584 per person
$1,584
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
You need more dinner options in hotel

Reviewed on Jan 17, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $584, price is now $336 per person
$336
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
We loved our stay at Hotel St. James and the location was perfect for our trip itinerary! The room was clean and spacious, and staff were friendly during our brief interactions. I will definitely stay here again and am looking forward to our next trip.

Reviewed on Jan 19, 2026

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
Price was $1,589, price is now $928 per person
$928
per person
Apr 4 - Apr 11
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (27 reviews)
Super clean, staff was lovely and welcoming.

Reviewed on Jan 15, 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 Jan 20 to Jan 21
$553 total
Jan 20 - Jan 21
Total with taxes and fees
9.4/10 Exceptional! (41 reviews)
Excellent

Reviewed on Dec 14, 2025

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
$89 nightly
The price is $101 total per night from Feb 4 to Feb 5
$101 total
Feb 4 - Feb 5
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Very nice room. The amenities were great. I would love to book in the future.

Reviewed on Jan 18, 2026

Courtyard by Marriott Poughkeepsie
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE Hyde Park NY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $163 total per night from Jan 29 to Jan 30
$163 total
Jan 29 - Jan 30
Total with taxes and fees
9.6/10 Exceptional! (454 reviews)
Wonderful stay. Would recommend.

Reviewed on Jan 13, 2026

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,131 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 $282 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.