Ashley Falls Vacations from $206

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The Latest Ashley Falls vacation packages

Price found within the past 48 hours. Click for updated prices.
SunView Motel
Catskills Retreat w/ Hot Tub, Fire Pit, Pool & Mtn Views The Windham Mountain House by Avantstay
AutoCamp Catskills
Coldbrook Bed and Breakfast
Woodstock Way Hotel
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Ashley Falls Hotel Deals

The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA
10/10 Exceptional! (14 reviews)
Nick and Tiffany were very welcoming and made check-in, check-out and everything in between very easy and seamless. The Blue Elm is a very comfortable cottage and we loved the historic elements that were used. we completely enjoyed our stay there and will stay again when we return to the area to ...

Reviewed on Nov 23, 2025

The Blue Elm - A Historic Berkshire Cottage
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
$184 nightly
The price is $206 total per night from Dec 21 to Dec 22
$206 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.

Reviewed on Nov 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 refundable
$119 nightly
The price is $133 total per night from Dec 1 to Dec 2
$133 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (789 reviews)
We loved the room!! Very comfy bed !

Reviewed on Nov 22, 2025

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