Milan Vacations from $579

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Your Milan Vacation

When a fun city break is calling, answer it with a vacation package to Milan. The neighborhood of Kingston Stockade District, which is good for families, festivals and markets, makes a wonderful base for your adventures. When it's time to go out and explore, be sure to put Old Rhinebeck Aerodrome and Red Hook Golf Club on the to-do list for your trip to Milan. Whoever you're escaping with and whatever you want to spend, your dream Milan vacation is just clicks away with Expedia.

The Latest Milan vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
Price was $888, price is now $579 per person
$579
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
7.6/10 Good! (558 reviews)
Excellent location!!

Reviewed on Dec 26, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,298, price is now $882 per person
$882
per person
Mar 15 - Mar 20
found 14 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Dewey

The Dewey

3.5 out of 5
Price was $932, price is now $686 per person
$686
per person
Mar 15 - Mar 20
found 14 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,107, price is now $818 per person
$818
per person
Mar 15 - Mar 20
found 14 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff was very welcoming and attentive. Room was clean.

Reviewed on Jan 3, 2026

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5
Save 100% on your flight
Price was $4,084, price is now $3,144 per person
$3,144
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Albany (ALB)
No reviews
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Discover the most popular places to visit in Milan

Old Rhinebeck Aerodrome

You can browse the exhibits at Old Rhinebeck Aerodrome, a museum with a story of its own, during your travels to Red Hook. Stroll along the marina or experience the area's festivals.

Old Rhinebeck Aerodrome

Milan Hotel Deals

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Jan 19 to Jan 20
$143 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (821 reviews)
You can tell they take care of the property

Reviewed on Jan 7, 2026

Residence Inn by Marriott Kingston
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $184 total per night from Feb 1 to Feb 2
$184 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (446 reviews)
Fun relaxing place friendly staff I will say plan accordingly on food. Their restaurant is not really a restaurant the options are really limited but the great thing is door dash and uber eats deliver there and it’s a good amount of restaurants not too far away.

Reviewed on Jan 5, 2026

AutoCamp Catskills
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 25 to Jan 26
$163 total
Jan 25 - Jan 26
Total with taxes and fees
9.6/10 Exceptional! (452 reviews)
The Christmas suite was so cute! Everything was clean and perfect.

Reviewed on Jan 12, 2026

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,195 properties in Milan
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 Milan Vacation Packages

Milan Essential Information

Language
English
Currency
U.S dollars
Top Sights
Old Rhinebeck Aerodrome, Poets Walk Park and Red Hook Golf Club

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Frequently asked questions

How much does a Milan vacation package cost?
You can grab a vacation package to this destination from $579 on Expedia. But how much your vacation to Milan costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Milan?
You can usually find lower rates and greater availability in December, January and February. Check out our cheap Milan vacation packages and you could land some great off-season deals.
How many days is enough for Milan?
Typically, a handful of days is enough to see the top attractions during your Milan vacation. However, if you want to have some time to relax or take day trips, consider extending your itinerary.
How to find the best Milan package deals?
Begin your search for a Milan package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Milan package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Milan escape underway.
Is it cheaper to book a Milan vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Milan trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Milan?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Milan trip.
Does Expedia offer Book Now, Pay Later Milan vacation packages?
Jet off on your dream escape to Milan with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.