Search Cheap Flights to
Ashland

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Ashland Flights as Low as $103

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

Breeze Airways
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 10 hours ago
$103
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 30, priced at $103 found 10 hours ago
Spirit Airlines
Wed, Sep 3 - Sun, Sep 7
MCO
Orlando Intl.
BOS
Logan Intl.
$104 Roundtrip, found 5 days ago
$104
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Logan Intl., returning Sun, Sep 7, priced at $104 found 5 days ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 6 hours ago
$107
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $107 found 6 hours ago
Spirit Airlines
Wed, Sep 10 - Fri, Sep 12
MCO
Orlando Intl.
BOS
Logan Intl.
$108 Roundtrip, found 4 hours ago
$108
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Orlando Intl. to Logan Intl., returning Fri, Sep 12, priced at $108 found 4 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 10 hours ago
$112
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $112 found 10 hours ago
Breeze Airways
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 10 hours ago
$113
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 30, priced at $113 found 10 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 10 hours ago
$117
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $117 found 10 hours ago
Spirit Airlines
Sat, Oct 11 - Sat, Oct 18
MCO
Orlando Intl.
BOS
Logan Intl.
$120 Roundtrip, found 4 hours ago
$120
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Oct 11 from Orlando Intl. to Logan Intl., returning Sat, Oct 18, priced at $120 found 4 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 10 hours ago
$122
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $122 found 10 hours ago
Frontier Airlines
Mon, Nov 3 - Mon, Nov 10
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Orlando Intl. to Logan Intl., returning Mon, Nov 10, priced at $126 found 1 day ago
JetBlue Airways
Tue, Oct 14 - Tue, Oct 14
MCO
Orlando Intl.
BOS
Logan Intl.
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Oct 14 from Orlando Intl. to Logan Intl., returning Tue, Oct 14, priced at $173 found 4 hours ago
United
Tue, Nov 4 - Tue, Nov 11
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Tue, Nov 11, priced at $197 found 10 hours ago
Delta
Wed, Oct 15 - Wed, Oct 15
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Oct 15 from Orlando Intl. to Logan Intl., returning Wed, Oct 15, priced at $197 found 4 hours ago
American Airlines
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
BOS
Logan Intl.
$217 Roundtrip, found 6 hours ago
$217
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Orlando Intl. to Logan Intl., returning Wed, Oct 22, priced at $217 found 6 hours ago
JetBlue Airways
Thu, Aug 21 - Tue, Aug 26
MCO
Orlando Intl.
ORH
Worcester Regional
$273 Roundtrip, found 14 hours ago
$273
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Thu, Aug 21 from Orlando Intl. to Worcester Regional, returning Tue, Aug 26, priced at $273 found 14 hours ago
American Airlines
Sat, Aug 16 - Mon, Aug 18
PIA
Greater Peoria Regional
ORH
Worcester Regional
$443 Roundtrip, found 8 hours ago
$443
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Greater Peoria Regional to Worcester Regional, returning Mon, Aug 18, priced at $443 found 8 hours 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 August, 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 $103, 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 $103 right now, why wait?

Ashland Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$102

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! (1,577 reviews)
"great area and front person support was great!"

Reviewed on Aug 9, 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! (2,089 reviews)
"Great view from the room, easy to walk along the river and to other sites."

Reviewed on Aug 9, 2025

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Hyatt Regency Boston/Cambridge
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! (3,795 reviews)
Copley Sq Hotel
"Overall great but I wouldn’t be able to do more than a night based on my experience. The biggest issues were: • no outlets in the bathroom • very poor water pressure and no actual shower head - just tub fill and a handheld option that’s bolstered lower on the wall • mattress ok not the most comfortable ..."

Reviewed on Aug 11, 2025

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Copley Square Hotel, a FOUND Hotel
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! (3,313 reviews)
"We were there to see Fenway ~ caught a couple games. Good walking distance but is residential so it’s clean and quiet. Highly recommend if going to Boston for the Red Sox! Hotel seemed understaffed at the front desk ~ staff there are working hard though."

Reviewed on Aug 10, 2025

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The Arcadian 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! (1,005 reviews)
"Confortable beds and nice bathroom. Great hotel close to Harvard."

Reviewed on Aug 11, 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 ...
8.4/10 Very Good! (1,737 reviews)
"Walkability"

Reviewed on Aug 8, 2025

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Sheraton Boston, a Marriott Hotel
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
400 Soldiers Field Road, Boston, MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,003 reviews)
"There are many restaurants close to the hotel."

Reviewed on Aug 10, 2025

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DoubleTree Suites by Hilton Hotel 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! (1,657 reviews)
"I have stayed at the Copley many times, but not since the lobby was renovated. The refresh looks great. If you are looking to stay in the Back Bay, this location can't be beat. You can use to 2 attached malls as shortcuts to stay out of the weather if necessary, and it connects all the way to the ..."

Reviewed on Aug 11, 2025

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Boston Marriott Copley Place
See all 1,886 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.