Ashley Falls Vacations from $937

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The Latest Ashley Falls vacation packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
The Haüs Windham
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
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Stay near popular Ashley Falls attractions

Ashley Falls 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
$203 nightly
The price is $227 total per night from Jul 13 to Jul 14
$227 total
Jul 13 - Jul 14
Total with taxes and fees
8.8/10 Excellent! (1,013 reviews)
"Clean room. Arrived late."

Reviewed on Jul 10, 2026

The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$118 nightly
The price is $132 total per night from Aug 2 to Aug 3
$132 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
"Excellent staff. Clean. Beds and towels excellent."

Reviewed on Jul 9, 2026

Quality Inn Great Barrington
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Fully refundable
$198 nightly
The price is $221 total per night from Jul 19 to Jul 20
$221 total
Jul 19 - Jul 20
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem ..."

Reviewed on Jul 11, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 Ashley Falls Vacation Packages

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Frequently asked questions

How to find the best Ashley Falls package deals?
Use Expedia's filters to find some unbeatable Ashley Falls package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Ashley Falls package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
When to book a vacation package to Ashley Falls?
If you have your Ashley Falls vacation dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.