Ashland Holidays

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    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

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

Top hotels in Ashland

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
The price is €133 per night from 28 Aug to 29 Aug
€133
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (730 reviews)
"Great location. Beautiful resort. Great and helpful staff"

Reviewed on 13 Aug 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
9.2/10 Wonderful! (613 reviews)
"Great location for hiking with close access to some restaurants. Staff was nice. Hotel was comfortable and clean."

Reviewed on 10 Aug 2025

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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
The price is €201 per night from 19 Aug to 20 Aug
€201
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (263 reviews)
"Great"

Reviewed on 11 Aug 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,584 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.

Frequently asked questions

How much does an Ashland holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Ashland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Ashland?
Plan your trip for the off-peak season and you're likely to get cheap Ashland holiday packages. Bear in mind that public holidays and major festivals and events can have an impact on prices, so do your research before booking.
How many days is enough for Ashland?
Generally, a handful of days is enough to go to the main attractions during your Ashland holiday. However, if you want to have more time to relax or take day tours, think about extending your trip.
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 customise your search by "Amenities," "Property type," "Traveller 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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Ashland?

  1. Choose your dates: The things you'd like to do in Ashland and your preferred season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Ashland.
  3. Decide how long to go for: Now that you're up to speed on Ashland, you can work out the perfect length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Ashland holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.