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Southeast Massachusetts

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Southeast Massachusetts Flights as Low as $107

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 6 hours ago
$107
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $107 found 6 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $108 found 6 hours ago
Breeze Airways
Fri, Jan 22 - Sun, Jan 24
RDU
Raleigh - Durham Intl.
PVD
T.F. Green
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 22 from Raleigh - Durham Intl. to T.F. Green, returning Sun, Jan 24, priced at $137 found 1 day ago
Delta
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 found 1 hour ago
American Airlines
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 found 1 hour ago
JetBlue Airways
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 found 1 hour ago
Breeze Airways
Sun, Dec 20 - Thu, Dec 24
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Dec 20 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Dec 24, priced at $178 found 5 days ago
Southwest Airlines
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $179 found 1 hour ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
MCO
Orlando Intl.
BOS
Logan Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Orlando Intl. to Logan Intl., returning Sat, Oct 24, priced at $192 found 1 day ago
United
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $199 found 1 hour ago
Bargain Flight
Mon, Nov 23 - Fri, Nov 27
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Mon, Nov 23 from Raleigh - Durham Intl. to Logan Intl., returning Fri, Nov 27, priced at $208 found 5 days ago
Breeze Airways
Sat, Oct 31 - Sat, Nov 14
MCO
Orlando Intl.
PVD
T.F. Green
$212 Roundtrip, found 3 hours ago
$212
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to T.F. Green, returning Sat, Nov 14, priced at $212 found 3 hours ago
Delta
Wed, Oct 7 - Tue, Oct 13
RDU
Raleigh - Durham Intl.
ORH
Worcester Regional
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 7 from Raleigh - Durham Intl. to Worcester Regional, returning Tue, Oct 13, priced at $367 found 2 days ago
Delta
Mon, Oct 5 - Tue, Oct 13
MCO
Orlando Intl.
ORH
Worcester Regional
$406 Roundtrip, found 4 days ago
$406
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 5 from Orlando Intl. to Worcester Regional, returning Tue, Oct 13, priced at $406 found 4 days ago
Alaska Airlines
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BOS
Logan Intl.
$533 Roundtrip, found 1 day ago
$533
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Logan Intl., returning Mon, Dec 7, priced at $533 found 1 day ago
American Airlines
Sat, Oct 3 - Tue, Oct 20
MCO
Orlando Intl.
HYA
Barnstable Municipal
$822 Roundtrip, found 5 days ago
$822
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Oct 3 from Orlando Intl. to Barnstable Municipal, returning Tue, Oct 20, priced at $822 found 5 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 November, 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 15 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 $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 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 $107 right now, why wait?

Southeast Massachusetts Flight Information
Destination airport
T.F. Green
Destination airport IATA code
PVD
Roundtrip price
$136

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 ...
7.8/10 Good! (1,233 reviews)
"My bathroom was dirty and the wood cabinets were falling apart."

Reviewed on Sep 26, 2026

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Best Western Adams Inn Quincy-Boston
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 ...
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Iris Hotel 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 breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,007 reviews)
"Property is compltely run down. Mold, cracked tiles, filthy tub and shower-head. The floor was sticky in the room. Trash (a lot) in the hallways. Carpets appeared to be 40 years old and in bad need of replacement or cleaning. Parking lot unlit with shady characters hanging on every corner. All around ..."

Reviewed on Sep 26, 2026

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Sonesta Select Boston Foxborough Mansfield
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
Lighthouse Inn

Lighthouse Inn

3 out of 5
1 Lighthouse Inn Rd West Dennis MA
Book a stay at this beach hotel in West Dennis. Enjoy free WiFi, free parking, and private plunge pools. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (324 reviews)
"The cottage style room was cute. We had a lovely fireplace which made our short stay complete since it was colder and windy. The staff and management were amazing! They helped us with firewood and were extremely friendly. We even played mini golf! It’s on the beach and a quiet location. It was minutes ..."

Reviewed on Sep 25, 2026

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Lighthouse Inn
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
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Chatham Bars Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
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Bayside Resort Hotel
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St Provincetown MA
Stay at this hotel in Provincetown. Enjoy free parking, an outdoor pool, and a fireplace in the lobby. Our guests praise the pool and the helpful staff in our ...
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Harbor Hotel Provincetown
See all 11,302 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. ...
8.8/10 Excellent! (1,002 reviews)
"Nice clean modern"

Reviewed on Sep 26, 2026

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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' ...
9.4/10 Exceptional! (19 reviews)
"Everything was even better than we'd hoped. The cottage was absolutely beautiful and extremely clean, and we couldn't have been in a better location! The view of the harbor, proximity to shopping and dining, and ease of check-in/out made for the perfect vacation. The bed was super comfy and the kitchen ..."

Reviewed on Sep 25, 2026

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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! (831 reviews)
"The lobby area was great. Although the room felt a bit sparse- seemed to be missing local charm. And we didn’t realize it was right at the end of the airport- we could have walked to it, instead we had a $23 taxi fee. The staff was outstanding- probably some of the warmest folks I have ever experienced. ..."

Reviewed on Sep 24, 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! (876 reviews)
"Clean and well maintained property. Rooms were large, clean, nicely maintained. The pool area was very inviting with plenty of lounge chairs, tables with umbrellas and chilled water. The continental breakfast had a nice variety of warm items along with fruit, yogurt, cereal and pastries. Very tasty! ..."

Reviewed on Sep 25, 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 ...
9.8/10 Exceptional! (87 reviews)
"Very nice BB with super owner. Rooms were very small and could be easily upgraded."

Reviewed on Sep 7, 2026

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The Inn at Cook Street
See all 11,302 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.