Search Cheap Flights to
Ashland

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Ashland Flights as Low as $102

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

Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $102 found 2 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $107 found 3 days ago
Spirit Airlines
Sat, Aug 23 - Sat, Aug 23
MCO
Orlando Intl.
BOS
Logan Intl.
$108 Roundtrip, found 21 hours ago
$108
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Orlando Intl. to Logan Intl., returning Sat, Aug 23, priced at $108 found 21 hours ago
Spirit Airlines
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
BOS
Logan Intl.
$109 Roundtrip, found 21 hours ago
$109
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Logan Intl., returning Sat, Aug 30, priced at $109 found 21 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $112 found 3 days ago
Spirit Airlines
Sun, Aug 31 - Sun, Aug 31
MCO
Orlando Intl.
BOS
Logan Intl.
$115 Roundtrip, found 21 hours ago
$115
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sun, Aug 31 from Orlando Intl. to Logan Intl., returning Sun, Aug 31, priced at $115 found 21 hours ago
Breeze Airways
Sat, Aug 23 - Sat, Aug 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Aug 23 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 23, priced at $117 found 4 days ago
Frontier Airlines
Fri, Aug 1 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$123 Roundtrip, found 3 days ago
$123
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 1 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $123 found 3 days ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 3 days ago
$126
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $126 found 3 days ago
Delta
Sat, Sep 13 - Tue, Sep 16
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 13 from Southwest Florida Intl. to Logan Intl., returning Tue, Sep 16, priced at $129 found 1 day ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $136 found 3 days ago
JetBlue Airways
Wed, Sep 10 - Mon, Sep 15
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Southwest Florida Intl. to Logan Intl., returning Mon, Sep 15, priced at $139 found 1 day ago
American Airlines
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
BOS
Logan Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Orlando Intl. to Logan Intl., returning Wed, Oct 22, priced at $171 found 2 hours ago
American Airlines
Tue, Aug 19 - Wed, Aug 20
MCO
Orlando Intl.
ORH
Worcester Regional
$181 Roundtrip, found 5 days ago
$181
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 19 from Orlando Intl. to Worcester Regional, returning Wed, Aug 20, priced at $181 found 5 days ago
United
Thu, Aug 21 - Wed, Aug 27
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$190 Roundtrip, found 5 days ago
$190
Roundtrip
found 5 days ago
Select United flight, departing Thu, Aug 21 from Southwest Florida Intl. to Logan Intl., returning Wed, Aug 27, priced at $190 found 5 days ago
American Airlines
Sun, Aug 3 - Wed, Aug 6
RSW
Southwest Florida Intl.
ORH
Worcester Regional
$306 Roundtrip, found 1 day ago
$306
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Aug 3 from Southwest Florida Intl. to Worcester Regional, returning Wed, Aug 6, priced at $306 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 ORH 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 October, 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 Norwood Memorial 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 $102, 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 $102 right now, why wait?

Ashland Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$101

Last Minute Hotel Deals in Ashland

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
9.2/10 Wonderful! (1,501 reviews)
"Very good location for a Red Sox game, close to Fenway and transportation and food options. Area is very safe, clean and well kept. The room was very small and the bed was pushed up against the wall making it hard to get in."

Reviewed on Jul 28, 2025

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citizenM Boston Back Bay
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the ...
8.4/10 Very Good! (3,790 reviews)
"The self parking was a little confusing but totally not on the hotel!! Next time I’d for sure go with valet. Because the hotel owns a night club you could hear the music from it but it personally wasn’t that bad. The room was clean and very cute! The night manager who checked us in was very ..."

Reviewed on Jul 26, 2025

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Copley Square Hotel, a FOUND Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (2,030 reviews)
"Solid hotel in a fabulous location on the Charles River in Cambridge. I was disappointed that since my last visit (pre-pandemic), they’ve closed the swimming pool and changed the restaurant menu from elevated to average. I’m still happy to stay there, but it’s no longer my favorite."

Reviewed on Jul 25, 2025

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Hyatt Regency Boston/Cambridge
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St, Brookline, MA
Stay at this 3.5-star hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (3,248 reviews)
"Hotel is 3 mile from downtown, tram stop right outside hotel very easy commute 25mins"

Reviewed on Jul 25, 2025

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The Arcadian Hotel
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
10 Huntington Ave, Boston, MA
Stay at this 4-star eco-certified hotel in Boston. Enjoy 4 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (1,329 reviews)
"Great staff and walkable"

Reviewed on Jul 21, 2025

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The Westin Copley Place, Boston, a Marriott Hotel
The Charles Hotel

The Charles Hotel

4 out of 5
One Bennett Street, Cambridge, MA
Stay at this 4-star luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,016 reviews)
"Beautiful and spacious accommodations convenient to the center if Cambridge and Harvard."

Reviewed on Jul 26, 2025

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The Charles Hotel
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

4 out of 5
39 Dalton St, Boston, MA
Book a stay at this eco-certified hotel in Boston. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
8.2/10 Very Good! (1,780 reviews)
"."

Reviewed on Jul 26, 2025

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Sheraton Boston, a Marriott Hotel
Boston Marriott Copley Place

Boston Marriott Copley Place

4 out of 5
110 Huntington Ave, Boston, MA
Stay at this 4-star business-friendly hotel in Boston. Enjoy 3 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (1,638 reviews)
"I liked the look of the property. I liked how bikeable the area was. It would be nice if they had a bathrobe and slippers. All in all I liked my experience there."

Reviewed on Jul 25, 2025

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Boston Marriott Copley Place
See all 1,862 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.