Millerton Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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!

Top Millerton Vacation Deals

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

Eastwind Windham

3.5 out of 5
Price was CA $907, price is now CA $837 per person
CA $837
per person
Sep 18 - Sep 20
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
9.2/10 Wonderful! (107 reviews)
Beautiful location. Really loved the full window ceiling in the cabin’s shower!

Reviewed on Jun 19, 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
Price was CA $2,184, price is now CA $1,833 per person
CA $1,833
per person
Sep 18 - Sep 20
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
No reviews

The Haüs Windham

The Haüs Windham

2 out of 5
Price was CA $1,152, price is now CA $1,033 per person
CA $1,033
per person
Sep 18 - Sep 20
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
7.6/10 Good! (29 reviews)

Hotel Vienna

Hotel Vienna

3 out of 5
Price was CA $910, price is now CA $849 per person
CA $849
per person
Sep 18 - Sep 20
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
9.4/10 Exceptional! (815 reviews)
All good ! Amazing staff!

Reviewed on Jul 2, 2026

Ready to book your vacation to Millerton?

 

Choose your dates

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
The price is CA $356 per night from Jul 5 to Jul 6
CA $356
CA $403 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (31 reviews)
"The hotel is beautiful, but unfortunately the restaurant was closed the night of our stay and we were disappointed because we planned on eating there. I guess I should have checked the restaurant hours before booking. Most of the town had businesses that were closed in the middle of the week, so ..."

Reviewed on Jul 3, 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
The price is CA $268 per night from Jul 22 to Jul 23
CA $268
CA $363 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Our room was very nice and the bed very comfortable. The hotel is a bit dated and could use updating. Overall it was a very enjoyable stay"

Reviewed on Jul 4, 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
The price is CA $282 per night from Jul 12 to Jul 13
CA $282
CA $319 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (915 reviews)
"Staff was kind, room was clean. Perfect location to explore the town and walk around."

Reviewed on Jul 3, 2026

Beekman Arms and Delamater Inn
See all 1,205 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.
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Stay near popular Millerton attractions

Harlem Valley Rail Trail

8.0/10 (2 reviews)
You can take time to visit Harlem Valley Rail Trail during your travels to Millerton. Discover the area's waterfalls and countryside.
See properties

Frequently asked questions

How much does a Millerton vacation package cost?
Offering excellent value package deals from CA $837 on Expedia, you'll be surprised at how little a vacation to Millerton costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Millerton?
January, February and March are the best times to look for cheap Millerton vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on hotels and flights.
How many days is enough for Millerton?
Generally, a handful of days is enough to explore the main sights during your Millerton vacation. But if you'd like to have more time to relax or go on day trips, think about extending your itinerary.
How to find the best Millerton package deals?
Use Expedia's handy filters to find some fabulous Millerton package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Millerton package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Millerton vacation as a package?
You can enjoy significant savings on your next Millerton getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Millerton?
If you have your Millerton travel dates confirmed, book as early as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Millerton?

  1. Choose your dates: The things you plan to do in Millerton and your favourite season can help you decide when to travel.
  2. Plan your budget wisely: On top of the price of your hotel, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that could arise during your trip to Millerton.
  3. Decide how long to go away for: Now that you're more familiar with Millerton, you can figure out the ideal length of your vacation. Put together a rough plan and give yourself enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the ideal Millerton vacation package for you.

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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.