Milton Vacations from $510

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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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $912, price is now $510 per person
$510
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,376, price is now $734 per person
$734
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,140 reviews)
Great! We love this place.

Reviewed on Oct 22, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,747, price is now $943 per person
$943
per person
Dec 26 - Jan 2
found 8 hours ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
8.4/10 Very Good! (579 reviews)
Way too overpriced for what you get! Let’s start with the positives. A magnificent view and a decent bed… The rooms are less than average, with terrible decor, and very noisy, to the point that we could hear clearly the couple next door for the whole night…. just like a cheap motel, except that it costs us almost $800 for the night.

Reviewed on Oct 5, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was $3,141, price is now $1,711 per person
$1,711
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (151 reviews)
A perfect place to stay!!

Reviewed on Sep 20, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $1,579, price is now $886 per person
$886
per person
Dec 26 - Jan 2
found 8 hours ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
8.4/10 Very Good! (143 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

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Milton Hotel Deals

Buttermilk Falls Inn

Buttermilk Falls Inn

3 out of 5
220 N Rd, Milton, NY
$482 nightly
The price is $540 total per night from Nov 4 to Nov 5
$540 total
Nov 4 - Nov 5
Total with taxes and fees
9.4/10 Exceptional! (35 reviews)
IThe inn was quaint and inviting. The staff was friendly and professional. The spa experience was wonderful!

Reviewed on Oct 13, 2025

Buttermilk Falls Inn
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night from Oct 26 to Oct 27
$129 total
Oct 26 - Oct 27
Total with taxes and fees
7/10 Good! (638 reviews)
Location was good and staff was friendly

Reviewed on Oct 23, 2025

The Crossroads Hotel, Newburgh
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
$110 nightly
The price is $128 total per night from Nov 2 to Nov 3
$128 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,038 reviews)
I can not say enough about the staff. They were friendly, funny, kind, attentive, helpful and competent. I did not have high expectations of our stay. I needed a safe, clean place for a one night stay with my two young kids and did not want to pay a fortune. But I was very surprised at the quality ...

Reviewed on Oct 20, 2025

Hampton Inn & Suites Poughkeepsie
See all 1,112 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 $510 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.