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Ashland

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Ashland Flights as Low as $149

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$149 Roundtrip, found 5 days ago
$149
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $149 found 5 days ago
Breeze Airways
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Stewart Intl., returning Sun, Jun 15, priced at $150 found 1 day ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $154 found 5 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $159 found 5 days ago
Breeze Airways
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Stewart Intl., returning Sun, Jun 15, priced at $160 found 1 day ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $164 found 5 days ago
Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 2 hours ago
$185
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $185 found 2 hours ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $187 found 1 day ago
Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $190 found 2 hours ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $192 found 1 day ago
Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 2 hours ago
$195
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $195 found 2 hours ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $197 found 1 day ago
Breeze Airways
Mon, Dec 8 - Thu, Dec 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Dec 8 from Orlando Intl. to Stewart Intl., returning Thu, Dec 11, priced at $199 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $201 found 1 day ago
Breeze Airways
Mon, Dec 8 - Thu, Dec 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Dec 8 from Orlando Intl. to Stewart Intl., returning Thu, Dec 11, priced at $204 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $206 found 1 day ago

Cheap Flights to Ashland

Fall in love at first flight with your vacation to Ashland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Ashland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Ashland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Ashland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Ashland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the null airport.

What is the cheapest month to fly to Ashland?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Ashland are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Ashland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Ashland.

What airport is best to fly into Ashland?

When you’re planning your trip to Ashland, convenience is the name of the game. Luckily, Ashland Columbia County Airport is nearby so you can deplane and get going on checking off everything on your Ashland must-do list.

How much are flights to Ashland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Ashland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $149, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Ashland?

The trick to saving a stack of cash on your flight to Ashland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $149 right now, why wait?

Ashland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$148

Last Minute Hotel Deals in Ashland

Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark
3 out of 5
7433 Main St, Hunter, NY
Stay at this 3-star hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.2/10 Wonderful! (639 reviews)
"Loved our stay. The rooms are large, freshly renovated, stylish and affordable. We loved being able to see the mountains directly from our window. They also have a lovely restaurant and library. I’m surprised they don’t host events."

Reviewed on May 4, 2025

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Hunter Lodge, a Bluebird by Lark
The Roxbury at Stratton Falls
The Roxbury at Stratton Falls
2 out of 5
48 Co Rd 41, Roxbury, NY
Stay at this hotel in Roxbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Plattekill State Forest and Plattekill Mountain are located ...
9.6/10 Exceptional! (24 reviews)
"One of the most unique lodging experiences you will ever have. 10/10, fantastic, blow your mind, etc. etc. Staff was great/friendly and very helpful. Pick your favorite theme and have a blast."

Reviewed on May 11, 2025

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The Roxbury at Stratton Falls
Urban Cowboy Lodge
Urban Cowboy Lodge
5 out of 5
37 Alpine Rd, Big Indian, NY
Stay at this 5-star luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (136 reviews)
"Beautiful property and amazing staff. We had a great time. Thank you"

Reviewed on May 11, 2025

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Urban Cowboy Lodge
Eastwind Windham
Eastwind Windham
2 out of 5
5088 NY-23, Windham, NY
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club ...
9.2/10 Wonderful! (53 reviews)
"Very lo-fi and bare bones, but well-designed and properly thought-out. Just what city hipster ski bums are looking for."

Reviewed on Mar 16, 2025

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Eastwind Windham
Hotel Mountain Brook
Hotel Mountain Brook
4 out of 5
57 Route 23c, Tannersville, NY
Stay at this 4-star hotel in Tannersville. Enjoy free breakfast, free parking, and cable TV channels. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (476 reviews)
"great stay"

Reviewed on Apr 21, 2025

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Hotel Mountain Brook
Wylder Hotel Windham
Wylder Hotel Windham
3.5 out of 5
19 New York 296, Windham, NY
Stay at this 3.5-star hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club ...
8.2/10 Very Good! (55 reviews)
"All was nice, very nice staff esp the bartender Chris! We could not get the TV’s to work in either room with the required logins, and the water took a really long time to get warm for the showers. Otherwise, really all fine and bucolic."

Reviewed on May 11, 2025

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Wylder Hotel Windham
Kaatskill Mountain Club at Hunter Mountain
Kaatskill Mountain Club at Hunter Mountain
2 out of 5
61 LIFTSIDE DR, Hunter, NY
Stay at this hotel in Hunter. Enjoy free WiFi, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Hunter ...
9/10 Wonderful! (233 reviews)
"I have read a lot of reviews on this property and I always try to steer clear of the bad reviews to let myself in on the experience so I can find out When you speak on “updating” and such, you must keep in mind the Nostalgia of this sport and what this mountain has down to maintain the East Coast ..."

Reviewed on Mar 21, 2025

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Kaatskill Mountain Club at Hunter Mountain
Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (557 reviews)
"It was beautiful stay nice clean and staff was very friendly and welcoming I would go again!"

Reviewed on May 12, 2025

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Hotel Vienna
See all 1,534 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.