Ashland Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Ashland Hotel Deals

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
$177 nightly
The price is $191 total per night from Aug 11 to Aug 12
$191 total
Aug 11 - Aug 12
Total includes taxes and fees
9.2/10 Wonderful! (722 reviews)
"Overall is excellent."

Reviewed on Aug 5, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $132 total per night from Sep 8 to Sep 9
$132 total
Sep 8 - Sep 9
Total includes taxes and fees
9.2/10 Wonderful! (606 reviews)
"One of the nicest places we’ve stayed. The description matched the experience and it was a true pleasure. We would recommend staying and wished we had time to stay longer. Lots of delicious options for breakfast. Very comfortable room. Nearby restaurants and very peaceful location. The staff were ..."

Reviewed on Aug 6, 2025

Hotel Vienna
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR, Hunter, NY
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $235 total per night from Aug 13 to Aug 14
$235 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (259 reviews)
"Front desk staff was really pleasant when checking in! The rooms felt a bit dated, but everything was nice and clean!"

Reviewed on Aug 4, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,572 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.