Ashland Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.681.983 ₫ per night from 16 Aug to 17 Aug
3.681.983 ₫
4.543.606 ₫ total
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Breakfast set up was very nice - needs to start at 7:00 am"

Reviewed on 11 Jul 2026

Hunter Lodge, a Bluebird by Lark
Emerson Resort & Spa

Emerson Resort & Spa

3.5 out of 5
5340 NY-28 Mount Tremper NY
The price is 5.775.660 ₫ per night from 5 Aug to 6 Aug
5.775.660 ₫
6.468.739 ₫ total
5 Aug - 6 Aug
includes taxes & fees
9.2/10 Wonderful! (80 reviews)
"Great place! Wish we could have stayed longer. Great breakfast!"

Reviewed on 7 Jul 2026

Emerson Resort & Spa
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

2 out of 5
61 LIFTSIDE DR Hunter NY
Fully refundableReserve now, pay when you stay
The price is 5.095.443 ₫ per night from 22 Jul to 23 Jul
5.095.443 ₫
6.067.517 ₫ total
22 Jul - 23 Jul
includes taxes & fees
9.2/10 Wonderful! (387 reviews)
"We enjoyed the pool and hot tubs"

Reviewed on 13 Jul 2026

Kaatskill Mountain Club & Condos by Vail Resorts
See all 1,649 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.

Stay near popular Ashland attractions

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?
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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.

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