Search Cheap Flights to
Rockland

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Rockland Flights as Low as $105

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

Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$105 Roundtrip, found 18 hours ago
$105
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $105 found 18 hours ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, found 18 hours ago
$109
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $109 found 18 hours ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 18 hours ago
$110
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $110 found 18 hours ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$115 Roundtrip, found 18 hours ago
$115
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $115 found 18 hours ago
Breeze Airways
Wed, May 28 - Wed, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Portsmouth Intl., returning Wed, Jun 4, priced at $119 found 1 day ago
Breeze Airways
Wed, May 28 - Wed, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$124 Roundtrip, found 9 hours ago
$124
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Portsmouth Intl., returning Wed, Jun 4, priced at $124 found 9 hours ago
Breeze Airways
Wed, May 28 - Wed, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$129 Roundtrip, found 9 hours ago
$129
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Portsmouth Intl., returning Wed, Jun 4, priced at $129 found 9 hours ago
Spirit Airlines
Tue, Jun 3 - Tue, Jun 3
MCO
Orlando Intl.
BOS
Logan Intl.
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Orlando Intl. to Logan Intl., returning Tue, Jun 3, priced at $132 found 5 days ago
Breeze Airways
Wed, May 28 - Wed, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$134 Roundtrip, found 9 hours ago
$134
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Portsmouth Intl., returning Wed, Jun 4, priced at $134 found 9 hours ago
Frontier Airlines
Mon, Jun 2 - Fri, Jun 13
MCO
Orlando Intl.
BOS
Logan Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Orlando Intl. to Logan Intl., returning Fri, Jun 13, priced at $137 found 5 days ago
Spirit Airlines
Tue, Jun 3 - Wed, Jun 4
MCO
Orlando Intl.
BOS
Logan Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Orlando Intl. to Logan Intl., returning Wed, Jun 4, priced at $147 found 4 days ago
Spirit Airlines
Mon, Jun 2 - Mon, Jun 2
MCO
Orlando Intl.
BOS
Logan Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Jun 2 from Orlando Intl. to Logan Intl., returning Mon, Jun 2, priced at $152 found 3 days ago
Bargain Flight
Mon, Jun 2 - Fri, Jun 6
MCO
Orlando Intl.
BOS
Logan Intl.
$213 Roundtrip, just found
$213
Roundtrip
just found
Select Bargain Flight flight, departing Mon, Jun 2 from Orlando Intl. to Logan Intl., returning Fri, Jun 6, priced at $213 just found
United
Fri, Jul 11 - Mon, Jul 14
MCO
Orlando Intl.
BOS
Logan Intl.
$220 Roundtrip, found 11 hours ago
$220
Roundtrip
found 11 hours ago
Select United flight, departing Fri, Jul 11 from Orlando Intl. to Logan Intl., returning Mon, Jul 14, priced at $220 found 11 hours ago
American Airlines
Mon, Jul 21 - Sat, Jul 26
MCO
Orlando Intl.
BOS
Logan Intl.
$220 Roundtrip, found 7 hours ago
$220
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Jul 21 from Orlando Intl. to Logan Intl., returning Sat, Jul 26, priced at $220 found 7 hours ago
JetBlue Airways
Mon, Jul 21 - Sat, Jul 26
MCO
Orlando Intl.
BOS
Logan Intl.
$231 Roundtrip, found 7 hours ago
$231
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Mon, Jul 21 from Orlando Intl. to Logan Intl., returning Sat, Jul 26, priced at $231 found 7 hours ago

Cheap Flights to Rockland

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

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

Frequently Asked Questions About flights to Rockland

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

What is the cheapest month to fly to Rockland?

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 Rockland are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Rockland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Rockland.

What airport is best to fly into Rockland?

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

How much are flights to Rockland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Rockland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $105, 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 Rockland?

The trick to saving a stack of cash on your flight to Rockland? 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 $105 right now, why wait?

Rockland Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$105

Last Minute Hotel Deals in Rockland

YOTEL Boston
YOTEL Boston
4 out of 5
65 Seaport Blvd, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular ...
8.4/10 Very Good! (2,030 reviews)
"Even though the rooms are small they are quite utilitarian and comfortable."

Reviewed on May 22, 2025

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YOTEL Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
8.2/10 Very Good! (3,284 reviews)
"I have often stayed here. It is a dependable hotel, that is very welcoming to its guests."

Reviewed on May 21, 2025

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Hilton Boston Park Plaza
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
9.2/10 Wonderful! (5,844 reviews)
"Beautiful property with helpful staff. Comfortable beds! We loved our stay and can’t wait to go back!"

Reviewed on May 21, 2025

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The Dagny Boston
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 ...
9.4/10 Exceptional! (1,173 reviews)
Fantastic Location, Cozy Accommodations
"We stayed at citizenM Back Bay for a quick trip to Boston. The location was fantastic. We could easily walk to Fenway and Northeastern. Although the room was extremely small, (I believe 150sf,) the space was well laid out and efficient. The bed was very comfortable. There was no parking on site and ..."

Reviewed on May 22, 2025

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citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...
9/10 Wonderful! (5,145 reviews)
"Great location. T blue line aquarium in front of the hotel. 2 stops from the airport. We had a room with a window. Clean, roomy. Most attractions walkable ( within 30 min walk) or easy reachable with the T and a short walk. Safe and clean neighborhood."

Reviewed on May 21, 2025

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Harborside Inn Of Boston
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (2,026 reviews)
"Expedia price was too high and the cancellation policy charge seemed high. We had a problem with our flight from Spain and asked to rebook our room from May 7 to May 8 so there would not be a cancellation?"

Reviewed on May 21, 2025

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The Revolution 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! (1,115 reviews)
"Nice hotel, great staff, room was stuffy and smelled stale"

Reviewed on May 21, 2025

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Hilton Boston Back Bay
The Godfrey Hotel Boston
The Godfrey Hotel Boston
4 out of 5
505 Washington Street, Boston, MA
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (4,000 reviews)
"The location and friendly staff"

Reviewed on May 21, 2025

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The Godfrey Hotel Boston
See all 3,216 properties in Rockland
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.