Millerton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Brokaw

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    Save up to CA $1,096 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.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was CA $851, price is now CA $744 per person
CA $744
per person
Oct 2 - Oct 5
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9.2/10 Wonderful! (266 reviews)
Very convenient to hiking trails. Staff very friendly and helpful

Reviewed on Aug. 23, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was CA $1,417, price is now CA $1,087 per person
CA $1,087
per person
Oct 2 - Oct 5
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9/10 Wonderful! (411 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug. 7, 2025

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Price was CA $1,043, price is now CA $906 per person
CA $906
per person
Oct 2 - Oct 5
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9.2/10 Wonderful! (737 reviews)
Comfortable, clean room. Beautiful surroundings. Friendly, helpful staff.

Reviewed on Aug. 23, 2025

Couple s Oasis Pool Stream Firepit Steam Room

Couple s Oasis Pool Stream Firepit Steam Room

2 out of 5
Price was CA $1,367, price is now CA $1,252 per person
CA $1,252
per person
Oct 2 - Oct 5
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
No reviews
Overlook Hotel

Overlook Hotel

2 out of 5
Price was CA $1,093, price is now CA $1,011 per person
CA $1,011
per person
Oct 2 - Oct 5
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
7.8/10 Good! (7 reviews)

Ready to book your vacation to Millerton?

 

Choose your dates

Millerton Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 7 to Sep 8
CA $128
CA $143 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"nice place"

Reviewed on Aug. 18, 2025

Quality 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 $261 per night from Sep 10 to Sep 11
CA $261
CA $354 total
Sep 10 - Sep 11
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Typical issues with old properties: failing latches, old windows, broken or missing pavers. Excessive wait times. Mediocre food service at excessive prices. Pet-friendly accommodations are good and convenient. Location makes up for almost all failings."

Reviewed on Aug. 20, 2025

The Red Lion Inn
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 refundableReserve now, pay when you stay
The price is CA $127 per night from Sep 2 to Sep 3
CA $127
CA $161 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (703 reviews)
"Handicap accessible"

Reviewed on Aug. 22, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,161 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Millerton vacation package cost?
Offering excellent value package deals from CA $744 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.