Millerton Vacations from $1,043

Book a Hotel + Flight or Car together to unlock savings

Your Millerton Vacation

Lock in a Millerton vacation package that has only the things you need and nothing you don't. Good for dining, culture and shopping, think about basing yourself in the neighborhood of Canann Village Historic District. Every trip to Millerton should include a little sightseeing. Harlem Valley Rail Trail is a superb place to kick things off. Expedia is here to help you escape your daily routine. Tailor your vacation to Millerton to suit your style of travel, whatever that may be!

The Latest Millerton vacation packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,210, price is now $1,043 per person
$1,043
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
8.8/10 Excellent! (97 reviews)
Beautiful scenery and great staff

Reviewed on Mar 22, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $2,573, price is now $1,975 per person
$1,975
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
7.8/10 Good! (28 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.

Reviewed on Apr 20, 2026

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,558, price is now $1,965 per person
$1,965
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
No reviews
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Save 100% on your flight
Price was $3,635, price is now $3,046 per person
$3,046
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
No reviews
Red Feather Lodge

Red Feather Lodge

3 out of 5
Save 100% on your flight
Price was $4,685, price is now $4,123 per person
$4,123
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
No reviews
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Discover the most popular places to visit in Millerton

Harlem Valley Rail Trail

4/5(2 reviews)

You can take time to visit Harlem Valley Rail Trail during your travels to Millerton. Discover the area's waterfalls and countryside.

Harlem Valley Rail Trail

Millerton Hotel Deals

The Millerton Inn

The Millerton Inn

2 out of 5
53 Main St Millerton NY
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $269 total per night from May 18 to May 19
$269 total
May 18 - May 19
Total with taxes and fees
8.4/10 Very Good! (26 reviews)
Power outage caused stay to be cancelled at last minute

Reviewed on May 11, 2026

The Millerton Inn
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from May 27 to May 28
$208 total
May 27 - May 28
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
The staff is wonderful!

Reviewed on May 17, 2026

The Red Lion Inn
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $249 total per night from May 20 to May 21
$249 total
May 20 - May 21
Total with taxes and fees
8.4/10 Very Good! (885 reviews)
Breakfast is weak . Floor in room eas dirty

Reviewed on May 16, 2026

Beekman Arms and Delamater Inn
See all 1,202 properties in Millerton
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 Millerton Vacation Packages

Millerton Essential Information

Language
English
Currency
U.S dollars
Population
940
Top Sights
Millbrook Vineyards and Winery, Wings Castle and Trevor Zoo

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Frequently asked questions

How much does a Millerton vacation package cost?
You can snap up a vacation package to this popular destination from $1,043 on Expedia. But how much your vacation to Millerton costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Millerton?
If you're hoping to score a cheap Millerton vacation package, consider visiting in December, January and February. You'll generally find better prices on flights and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Millerton?
With a well-organized schedule, you can easily tick off the most popular Millerton sights in a handful of days. But if you want to discover lesser-known spots or go on day tours, think about booking your Millerton vacation for longer.
How to find the best Millerton package deals?
Finding a cheap Millerton package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Millerton package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Millerton vacation as a package?
You can enjoy significant savings on your next Millerton escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Millerton?
Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Millerton getaway.
Does Expedia offer Book Now, Pay Later Millerton vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Millerton trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.