Ashland Vacations from $398

Book a Hotel + Flight or Car together to unlock savings

The Latest Ashland vacation packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $478, price is now $398 per person
$398
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
18/10 Exceptional! (430 reviews)
Great location. Amazing views.

Reviewed on Nov 15, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Price was $773, price is now $644 per person
$644
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
19.2/10 Exceptional! (205 reviews)
Fortunately it was in the fall and with some leaves already down the gorgeous stream was visible. I highly recommend this property

Reviewed on Nov 10, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $890, price is now $760 per person
$760
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
17.2/10 Exceptional! (17 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!

Reviewed on Sep 15, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $587, price is now $533 per person
$533
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
17.6/10 Exceptional! (79 reviews)
Really nice restored resort. Rooms were great, staff was friendly. The food is very good.

Reviewed on Nov 3, 2025

The Herwood Inn

The Herwood Inn

4.5 out of 5
Price was $528, price is now $487 per person
$487
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
19.2/10 Exceptional! (89 reviews)
Just lovely all around! I loved the attention to detail inside and on the grounds.

Reviewed on Oct 1, 2025

Don't see what you're looking for?
See all available trips from Columbus to Ashland
View all trips

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
$188 nightly
The price is $203 total per night from Nov 23 to Nov 24
$203 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (807 reviews)
Easy and quick transaction

Reviewed on Nov 13, 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
$111 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (700 reviews)
Clean room

Reviewed on Nov 14, 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 Nov 18 to Nov 19
$235 total
Nov 18 - Nov 19
Total with taxes and fees
9.2/10 Wonderful! (314 reviews)
228

Reviewed on Nov 11, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,596 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.

Find the Best Ashland Vacation Packages

Ashland Essential Information

Language
English
Currency
U.S dollars
Top Sights
Hunter Mountain and Zoom Flume

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 from $398 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.