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Sterling

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Sterling 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 13 hours ago
$102
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 $102 found 13 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 5 days ago
$107
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $107 found 5 days ago
Spirit Airlines
Sat, Aug 23 - Sat, Aug 23
MCO
Orlando Intl.
BOS
Logan Intl.
$108 Roundtrip, found 15 hours ago
$108
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Orlando Intl. to Logan Intl., returning Sat, Aug 23, priced at $108 found 15 hours ago
Spirit Airlines
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
BOS
Logan Intl.
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Logan Intl., returning Sat, Aug 30, priced at $109 found 2 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $112 found 5 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $117 found 1 day ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $122 found 1 day ago
Frontier Airlines
Fri, Aug 1 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$123 Roundtrip, found 5 days ago
$123
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Aug 1 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $123 found 5 days ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $126 found 4 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 6 hours ago
$127
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $127 found 6 hours ago
Frontier Airlines
Fri, Aug 15 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$136 Roundtrip, found 4 days ago
$136
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $136 found 4 days ago
Delta
Tue, Nov 4 - Wed, Nov 12
MCO
Orlando Intl.
BOS
Logan Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Wed, Nov 12, priced at $157 found 4 hours ago
JetBlue Airways
Tue, Nov 4 - Wed, Nov 12
MCO
Orlando Intl.
BOS
Logan Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Wed, Nov 12, priced at $157 found 4 hours ago
American Airlines
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
BOS
Logan Intl.
$171 Roundtrip, found 13 hours ago
$171
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Orlando Intl. to Logan Intl., returning Wed, Oct 22, priced at $171 found 13 hours ago
Delta
Wed, Aug 20 - Thu, Aug 21
MCO
Orlando Intl.
ORH
Worcester Regional
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 20 from Orlando Intl. to Worcester Regional, returning Thu, Aug 21, priced at $195 found 5 days ago
United
Tue, Nov 4 - Wed, Nov 12
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select United flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Wed, Nov 12, priced at $197 found 4 hours ago

Cheap Flights to Sterling

Fall in love at first flight with your vacation to Sterling 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 Sterling on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Sterling

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Sterling 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 Sterling?

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 Sterling are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Sterling?

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 Sterling.

What airport is best to fly into Sterling?

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

How much are flights to Sterling?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Sterling 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 Sterling?

The trick to saving a stack of cash on your flight to Sterling? 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?

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

Last Minute Hotel Deals in Sterling

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road, Sterling, MA
Stay at this 3.5-star hotel in Sterling. Enjoy free WiFi, free parking, and room service. Popular attractions Mary Had a Little Lamb Statue and Davis' Farmland ...
8.6/10 Excellent! (132 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."

Reviewed on Jun 25, 2025

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Chocksett Inn and Restaurant
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd, Framingham, MA
Stay at this motel in Framingham. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,026 reviews)
"Fine but in decline . Could be better . I have no specific concerns"

Reviewed on Jul 26, 2025

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Motel 6 Framingham, MA - Boston West
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr, Westborough, MA
Stay at this 4-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,018 reviews)
"Great stay, location and breakfast!"

Reviewed on Jul 22, 2025

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DoubleTree by Hilton Hotel Boston - Westborough
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Stay at this 3.5-star family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,016 reviews)
"The staffs are friendly, the rooms are clean nice and spacious."

Reviewed on Jul 27, 2025

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Great Wolf Lodge Boston / Fitchburg, MA
Courtyard by Marriott Boston Natick

Courtyard by Marriott Boston Natick

3 out of 5
342 Speen St, Natick, MA
Stay at this 3-star business-friendly hotel in Natick. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,016 reviews)
"Clean room and friendly stuff"

Reviewed on Jul 24, 2025

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Courtyard by Marriott Boston Natick
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St, Natick, MA
Stay at this 3.5-star business-friendly hotel in Natick. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
"Great spot very convenient with access to major highways close by. Staff and hotel were very nice."

Reviewed on Jul 29, 2025

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The Verve Hotel Boston Natick, Tapestry Collection by Hilton
Best Western Royal Plaza Hotel & Trade Center

Best Western Royal Plaza Hotel & Trade Center

3 out of 5
181 Boston Post Rd W, Marlborough, MA
Book a stay at this business-friendly hotel in Marlborough. Enjoy free breakfast, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,014 reviews)
"Stay here for a hockey tournament it was big close to the rink but not exactly in the middle of the hoopla, leading to a quieter night and easier parking staff was great"

Reviewed on Jul 26, 2025

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Best Western Royal Plaza Hotel & Trade Center
Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

2.5 out of 5
1800 Computer Dr, Westborough, MA
Book a stay at this business-friendly hotel in Westborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.4/10 (904 reviews)
"Good"

Reviewed on Jul 18, 2025

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Extended Stay America Suites Boston Westborough Computer Dr
See all 354 properties in Sterling
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.