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Southeast Massachusetts

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Southeast Massachusetts Flights as Low as $148

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

Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $148 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $153 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $153 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $158 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $167 found 6 hours ago
Frontier Airlines
Mon, Sep 28 - Fri, Oct 2
MCO
Orlando Intl.
BOS
Logan Intl.
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Orlando Intl. to Logan Intl., returning Fri, Oct 2, priced at $170 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$172 Roundtrip, found 6 hours ago
$172
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $172 found 6 hours ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$173 Roundtrip, found 4 days ago
$173
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $173 found 4 days ago
JetBlue Airways
Tue, Oct 6 - Tue, Oct 6
MCO
Orlando Intl.
BOS
Logan Intl.
$183 Roundtrip, found 6 hours ago
$183
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Orlando Intl. to Logan Intl., returning Tue, Oct 6, priced at $183 found 6 hours ago
American Airlines
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 6 hours ago
$199
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $199 found 6 hours ago
Delta
Tue, Sep 29 - Sat, Oct 3
MCO
Orlando Intl.
BOS
Logan Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 29 from Orlando Intl. to Logan Intl., returning Sat, Oct 3, priced at $209 found 2 days ago
Breeze Airways
Mon, Aug 31 - Wed, Sep 2
MCO
Orlando Intl.
PVD
T.F. Green
$214 Roundtrip, found 3 days ago
$214
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Aug 31 from Orlando Intl. to T.F. Green, returning Wed, Sep 2, priced at $214 found 3 days ago
United
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$229 Roundtrip, found 6 hours ago
$229
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $229 found 6 hours ago
JetBlue Airways
Fri, Aug 28 - Wed, Sep 2
MCO
Orlando Intl.
ACK
Nantucket Memorial
$295 Roundtrip, found 5 hours ago
$295
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Fri, Aug 28 from Orlando Intl. to Nantucket Memorial, returning Wed, Sep 2, priced at $295 found 5 hours ago
Delta
Sun, Sep 6 - Fri, Sep 25
MCO
Orlando Intl.
MVY
Martha's Vineyard
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Sep 6 from Orlando Intl. to Martha's Vineyard, returning Fri, Sep 25, priced at $304 found 3 days ago
American Airlines
Tue, Jul 28 - Sat, Aug 1
MCO
Orlando Intl.
ORH
Worcester Regional
$428 Roundtrip, found 4 days ago
$428
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jul 28 from Orlando Intl. to Worcester Regional, returning Sat, Aug 1, priced at $428 found 4 days ago

Cheap Flights to Southeast Massachusetts

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

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

Frequently Asked Questions About flights to Southeast Massachusetts

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

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 Southeast Massachusetts are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Southeast Massachusetts?

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 Southeast Massachusetts.

What airport is best to fly into Southeast Massachusetts?

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

How much are flights to Southeast Massachusetts?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Southeast Massachusetts on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $148, 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 Southeast Massachusetts?

The trick to saving a stack of cash on your flight to Southeast Massachusetts? 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 $148 right now, why wait?

Southeast Massachusetts Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$117

Last Minute Hotel Deals in Southeast Massachusetts

Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston

2.5 out of 5
29 Hancock St Quincy MA
Book a stay at this business-friendly hotel in Quincy. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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Best Western Adams Inn Quincy-Boston
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
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Margaritaville Resort Cape Cod
Sonesta Select Boston Foxborough Mansfield

Sonesta Select Boston Foxborough Mansfield

3 out of 5
35 Foxborough Boulevard Foxborough MA
Book a stay at this business-friendly hotel in Foxborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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Sonesta Select Boston Foxborough Mansfield
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Book a stay at this business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woods Hole Ferry Terminal ...
8.6/10 Excellent! (299 reviews)
"Would have liked a map to the grounds. Forgot or didn’t know there was a pool. I asked about a dining room and was told no but it was obvious at breakfast they had one and a bar for the evening. Staff was helpful at recommending a dinner place offsite at checkin however. Staff Was not aware of ferry ..."

Reviewed on Jul 22, 2026

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Iris Hotel Cape Cod
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

4 out of 5
135 Route 28 West Yarmouth MA
Book a stay at this beach hotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. ...
9.4/10 Exceptional! (221 reviews)
"Beautiful room, grounds and pool!"

Reviewed on Jul 21, 2026

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Uncommoner Hotel by Reverie Boutique Collection
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28 West Yarmouth MA
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
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Cape Sands Inn
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Book a stay at this business-friendly hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,009 reviews)
"The motel was comfortable at a good price. Its located in a beutiful area you can walk to the bay."

Reviewed on Jul 21, 2026

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Falmouth Inn
Parker Beach Lodge

Parker Beach Lodge

3 out of 5
192 S Shore Dr South Yarmouth MA
Stay at this hotel in South Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (459 reviews)
"This place was just "alright" check in staff was helpful and kind but not worth what they're charging per night there. It's really just a cheap motel with white shutters posing as a seaside oasis. Granted it was high season, but still the price and all around feel of the place wasn't worth the nightly ..."

Reviewed on Jul 21, 2026

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Parker Beach Lodge
See all 11,520 properties in Southeast Massachusetts
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.

Top Hotels With Free Airport Shuttle

8 Dyer Hotel

8 Dyer Hotel

4 out of 5
8 Dyer Street Provincetown MA
Stay at this B&B in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Commercial Street and Packard Gallery are located ...
10/10 Exceptional! (18 reviews)
"Wonderful location- great hotel"

Reviewed on Feb 17, 2025

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8 Dyer Hotel
Hampton Inn & Suites Cape Cod-West Yarmouth

Hampton Inn & Suites Cape Cod-West Yarmouth

2.5 out of 5
99 Main Street, Route 28 West Yarmouth MA
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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Hampton Inn & Suites Cape Cod-West Yarmouth
Harborview Nantucket

Harborview Nantucket

4 out of 5
24 Washington Street Nantucket MA
Book a stay at this beach cottage in Nantucket. Enjoy free WiFi, a private beach, and a garden. Popular attractions Maria Mitchell Aquarium and The Artists' ...
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Harborview Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (744 reviews)
"There are too many negatives to comment on but here are a few. The fact that this hotel was rated 9.2 on Expedia is an absolute joke. On top of the poor quality, the room was more expensive than any hotel I have ever stayed in whether it was the Four Seasons in Maui or the Mandarin Oriental in London ..."

Reviewed on Jul 20, 2026

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Nantucket Inn
Seaglass Inn Provincetown

Seaglass Inn Provincetown

3 out of 5
105 Bradford Street Extension Provincetown MA
Stay at this hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
9.6/10 Exceptional! (844 reviews)
"The place was great from the moment I checked in. And although they say that they have a continental breakfast, it's better than that with tasty hot food too. Would stay again for sure."

Reviewed on Jul 21, 2026

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Seaglass Inn Provincetown
The Inn at Cook Street

The Inn at Cook Street

3 out of 5
7 Cook Street Provincetown MA
Book a stay at this beach B&B in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Commercial Street and Provincetown Art ...
10/10 Exceptional! (82 reviews)
"The Inn at Cook St is privately owned and well maintained by the owner Spencer. He greeted us and personally supervised where we safely parked our car, fix the television so we could watch the Knicks game and cooked the best breakfast ever! And he gardens too. It is worth every penny to stay at this ..."

Reviewed on Jun 10, 2026

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The Inn at Cook Street
See all 11,520 properties in Southeast Massachusetts
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.