Ashland Vacations

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Ashland Hotel Deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
$130 nightly
The price is $141 total per night from Oct 20 to Oct 21
$141 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (650 reviews)
"Location was perfect. Clean and quiet rooms, favorite was was the pool and sauna area. Would definitely stay here again"

Reviewed on Sep 27, 2025

Hotel Vienna
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $168 total per night from Oct 20 to Oct 21
$168 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (772 reviews)
"Clean and spacious, but missing artwork"

Reviewed on Sep 26, 2025

Hunter Lodge, a Bluebird by Lark
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR, Hunter, NY
$207 nightly
The price is $224 total per night from Oct 29 to Oct 30
$224 total
Oct 29 - Oct 30
Total with taxes and fees
9/10 Wonderful! (279 reviews)
"there was many amenities including a gym"

Reviewed on Sep 3, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,587 properties in Ashland
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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Frequently asked questions

How much does an Ashland vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Ashland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Ashland?
March, April and June are great times to look for cheap Ashland vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and hotels.
How many days is enough for Ashland?
Usually, a handful of days is enough to tick off the top sights during your Ashland vacation. But if you want to have some time to rest or go on day trips, consider extending your itinerary.
How to find the best Ashland package deals?
Finding a cheap Ashland package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most affordable Ashland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations individually. Better still, you can customize your Ashland getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Ashland?
If you're planning a spur-of-the-moment Ashland getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Ashland vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Ashland trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.