Search Cheap Flights to
Ashland

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Ashland Flights as Low as $107

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.
$107 Roundtrip, found 13 hours ago
$107
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $107 found 13 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 13 hours ago
$112
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $112 found 13 hours ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $117 found 13 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $122 found 13 hours ago
Breeze Airways
Wed, Dec 3 - Sat, Dec 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Dec 6, priced at $127 found 4 days ago
Spirit Airlines
Mon, Sep 15 - Sat, Sep 20
MCO
Orlando Intl.
BOS
Logan Intl.
$130 Roundtrip, found 5 hours ago
$130
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Mon, Sep 15 from Orlando Intl. to Logan Intl., returning Sat, Sep 20, priced at $130 found 5 hours ago
Spirit Airlines
Wed, Jul 30 - Thu, Jul 31
MCO
Orlando Intl.
BOS
Logan Intl.
$132 Roundtrip, found 7 hours ago
$132
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Orlando Intl. to Logan Intl., returning Thu, Jul 31, priced at $132 found 7 hours ago
Spirit Airlines
Sun, Sep 14 - Thu, Sep 18
MCO
Orlando Intl.
BOS
Logan Intl.
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Sep 14 from Orlando Intl. to Logan Intl., returning Thu, Sep 18, priced at $140 found 1 day ago
Spirit Airlines
Thu, Jul 17 - Fri, Jul 18
MCO
Orlando Intl.
BOS
Logan Intl.
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Jul 17 from Orlando Intl. to Logan Intl., returning Fri, Jul 18, priced at $143 found 1 day ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 3
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$143 Roundtrip, found 8 hours ago
$143
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 3, priced at $143 found 8 hours ago
JetBlue Airways
Tue, Aug 12 - Tue, Aug 12
MCO
Orlando Intl.
BOS
Logan Intl.
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Logan Intl., returning Tue, Aug 12, priced at $180 found 2 days ago
Frontier Airlines
Fri, Jul 18 - Sat, Jul 19
MCO
Orlando Intl.
BOS
Logan Intl.
$185 Roundtrip, found 13 hours ago
$185
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Orlando Intl. to Logan Intl., returning Sat, Jul 19, priced at $185 found 13 hours ago
United
Mon, Sep 15 - Sat, Sep 20
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select United flight, departing Mon, Sep 15 from Orlando Intl. to Logan Intl., returning Sat, Sep 20, priced at $197 found 5 hours ago
American Airlines
Fri, Jul 4 - Fri, Jul 4
MCO
Orlando Intl.
BOS
Logan Intl.
$202 Roundtrip, found 5 hours ago
$202
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Jul 4 from Orlando Intl. to Logan Intl., returning Fri, Jul 4, priced at $202 found 5 hours ago
Delta
Mon, Sep 15 - Sat, Sep 20
MCO
Orlando Intl.
BOS
Logan Intl.
$208 Roundtrip, found 5 hours ago
$208
Roundtrip
found 5 hours ago
Select Delta flight, departing Mon, Sep 15 from Orlando Intl. to Logan Intl., returning Sat, Sep 20, priced at $208 found 5 hours ago
American Airlines
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
ORH
Worcester Regional
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jun 20 from Orlando Intl. to Worcester Regional, returning Tue, Jun 24, priced at $241 found 5 days 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 $107, 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 $107 right now, why wait?

Ashland Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$106

Last Minute Hotel Deals in Ashland

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, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (3,688 reviews)
"Hotel was nice and clean, daily refresh of the room. Room a little tired looking with peeling wallpaper but good amentities including air con and in room fridge. Shower wasnt overly powerful."

Reviewed on Jun 11, 2025

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Copley Square Hotel, a FOUND Hotel
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,113 reviews)
"Great location, close to hub of Boston"

Reviewed on Jun 11, 2025

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Hilton Boston Back Bay
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! (1,245 reviews)
"Citizen M is my favorite property to stay at when solo traveling!"

Reviewed on Jun 12, 2025

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citizenM Boston Back Bay
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! (1,890 reviews)
"Great hotel. I didn't appreciate, however, being given a room with an obstructed view of the Charles River, and with a malfunctioning toilet that would not flush. Really?"

Reviewed on Jun 12, 2025

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Hyatt Regency Boston/Cambridge
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! (1,553 reviews)
"Marriott was within walking distance to the green line and orange line. Would highly recommend this hotel."

Reviewed on Jun 9, 2025

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Boston Marriott Copley Place
Embassy Suites by Hilton Boston Waltham
Embassy Suites by Hilton Boston Waltham
3.5 out of 5
550 Winter Street, Waltham, MA
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the breakfast ...
7.8/10 Good! (1,974 reviews)
"Beds are comfortable, it is clean enough , just a little tired looking, in need of an update."

Reviewed on Jun 14, 2025

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Embassy Suites by Hilton Boston Waltham
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! (3,097 reviews)
"This hotel was great for my visit. Located right next to a T stop. Hotel was clean and the staff was helpful. Breakfast was only ok."

Reviewed on Jun 14, 2025

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The Arcadian 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! (1,743 reviews)
"Good"

Reviewed on Jun 13, 2025

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Sheraton Boston, a Marriott Hotel
See all 1,816 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.