Millerton Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Brokaw

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!

Discover the most popular places to visit in Millerton

Harlem Valley Rail Trail

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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $198 total per night from Jan 26 to Jan 27
$198 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...

Reviewed on Dec 23, 2025

The Red Lion Inn
Beekman Arms Hotel

Beekman Arms Hotel

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Jan 1 to Jan 2
$127 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (810 reviews)
A beautiful hotel and we look forward to seeing it again when renovations are completed

Reviewed on Dec 14, 2025

Beekman Arms Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
$145 nightly
The price is $162 total per night from Jan 4 to Jan 5
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (808 reviews)
Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more.

Reviewed on Dec 24, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,166 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Millerton vacation package cost?
You can snap up a vacation package to this popular destination 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.