Cheap Flights to Western Massachusetts from $49

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How Much Does it Cost To Fly To Western Massachusetts?

The cheapest prices found with in the last 7 days for return flights were $112 and $49 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Jan 15 - Mon, Jan 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$112 Roundtrip, found 11 hours ago
$112
Roundtrip
found 11 hours ago
Select Allegiant Air flight, departing Fri, Jan 15 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Jan 18, priced at $112 found 11 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 31 to November 7$170
RSWWindsor LocksDecember 9 to December 13$193
JFKWindsor LocksOctober 15 to October 18$317
JFKLathamOctober 16 to October 22$323
RSWWorcesterNovember 13 to November 16$419
JFKWorcesterOctober 3 to October 10$582
MANWindsor LocksOctober 18 to October 22$1,043
MANLathamNovember 12 to December 3$1,117
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksSeptember 27 to October 1$347
RSWLathamSeptember 27 to October 6$439
JFKWindsor LocksSeptember 25 to September 27$494
RSWWorcesterSeptember 27 to October 1$653
JFKLathamSeptember 27 to October 26$674
*Prices include taxes and fees

Western Massachusetts Flight Information

Traveling to
Western Massachusetts
Lowest Price
$112
Number of Airlines Serving
Airlines Serving
Allegiant Air
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Western Massachusetts Accommodation Deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
$69 nightly
The price is $76 total per night from Sep 22 to Sep 23
$76 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.8/10 (1,001 reviews)
"Clean but old and warn. I can't complain, great for the money."

Reviewed on Sep 20, 2026

Opens in a new windowPleasant Valley Motel West Stockbridge
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street West Springfield MA
$103 nightly
The price is $117 total per night from Oct 4 to Oct 5
$117 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (1,003 reviews)
"The facility was supposed to be 100% smoke free but my room reeked of cigarettes. There was a dead fly on the floor that remained there the whole time I stayed. Not a good experience"

Reviewed on Sep 20, 2026

Opens in a new windowRed Roof Inn PLUS+ West Springfield
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd Lenox MA
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (641 reviews)
"We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it"

Reviewed on Oct 26, 2025

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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
8.2/10 Very Good! (455 reviews)
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

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Opens in a new windowLantern House Motel
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.

Luxury Hotels in Western Massachusetts

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$559 nightly
The price is $625 total per night from Oct 12 to Oct 13
$625 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
$140 nightly
The price is $157 total per night from Sep 22 to Sep 23
$157 total
Sep 22 - Sep 23
Total with taxes and fees
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowHotel Northampton
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
222 Adams Rd Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Colonial Plaza and Linear ...
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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
8.2/10 Very Good! (455 reviews)
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Get rates
Opens in a new windowLantern House Motel
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.

Family Friendly Hotels in Western Massachusetts

Vacation Village in the Berkshires
Great for families

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$122 nightly
The price is $136 total per night from Sep 22 to Sep 23
$136 total
Sep 22 - Sep 23
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,665 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...
"Excelente A+, lo recomiendo"

Reviewed on Sep 20, 2026

Opens in a new windowVacation Village in the Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA
Great for families

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
$122 nightly
The price is $139 total per night from Sep 28 to Sep 29
$139 total
Sep 28 - Sep 29
Total with taxes and fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,250 reviews)

Families like: Indoor pool, game room, cribs, free breakfast for the whole family

Travelers say...
"This was my family's 3rd or 4th time staying at this hotel & we love it. We'll keep going back. Its located on Congress Street in downtown Springfield, perfectly located 12 minutes from The Big E State Fair (which is primarily why we go to Springfield) but its also extremely close to The Basketball ..."

Reviewed on Sep 21, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$142 nightly
The price is $158 total per night from Sep 27 to Sep 28
$158 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this spa hotel in Holyoke. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,074 reviews)
"Everything was great! The only thing that was not so good was the elevator. It was so slow, and smelled like a litter box."

Reviewed on Sep 20, 2026

Opens in a new windowD. Hotel Suites & Spa
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Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
$101 nightly
The price is $116 total per night from Oct 11 to Oct 12
$116 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield ...
9.2/10 Wonderful! (334 reviews)
"The room was quiet. The room temperature was perfect. I was near the ice maker and didn't hear it. Very pleased with my stay."

Reviewed on Sep 20, 2026

Opens in a new windowBlue A Modern Hotel, an Ascend Collection Hotel
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.

Best Western Massachusetts Flight and Hotel Packages

Western Massachusetts flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $398, price is now $338 per person
$338
per person
Oct 23 - Oct 25
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Price was $564, price is now $463 per person
$463
per person
Oct 23 - Oct 25
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $428, price is now $371 per person
$371
per person
Oct 23 - Oct 25
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Orlando to Western Massachusetts
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Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

How much is the cheapest flight to Western Massachusetts?
Based on prices found over the last seven days, a roundtrip flight to Western Massachusetts was as low as $112. If you're flexible with your dates, it will be easy to land a great bargain. This price was available on Travelocity for flights to Western Massachusetts departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Western Massachusetts?
If you're thinking of booking a trip to Western Massachusetts, January is the cheapest time to fly there. This is based on Travelocity's direct return flight demand between January and December last year. Choose your dates and secure your spot today.
How can I check my flight status to Western Massachusetts?
Whether you'd like to view the status of your flight to Western Massachusetts or make changes to your itinerary, you'll find all the necessary details on our customer portal, Trips. Click on "Trips" at the top of our homepage, then log in or open a new account. Another convenient way to view and manage all your bookings is with the Travelocity app. Get real-time notifications about your flight and quickly share updates with any family flying with you.
How do I find the best deals on flights to Western Massachusetts?
Here are our tips — book early, avoid peak season and be flexible with your dates. If you don't have a specific date in mind, search for your flight to Western Massachusetts on Travelocity and click on "Flexible dates" above your results. This will help you locate any cheaper tickets on surrounding days. $112 was the most affordable price for a roundtrip flight to Western Massachusetts in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Western Massachusetts with Travelocity?
Search for cheap flights to Western Massachusetts with Travelocity and start packing for your next getaway. With 24/7 customer support during every step of your trip and our Price Match Guarantee, we take the difficulty out of finding cheap family flights, hotels, rental cars and more. Score a great deal today and brace yourself for an epic adventure.
What are the most popular flight routes to Western Massachusetts?
Browse through these major flight routes to Western Massachusetts and start planning your next vacation:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 3,514 flights a month.
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 3,419 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 3,193 flights a month.

How much is a flight to Western Massachusetts on average?
Airfares for roundtrip flights to Western Massachusetts were priced between $112 and $1,117 in the last seven days. As soon as you find a terrific deal, lock it in and get ready to jet off on your next fun adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Western Massachusetts?
The length of a direct flight to Western Massachusetts of course varies, but here are the average travel times for some common routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 2 hours and 23 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 51 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 2 hours and 56 minutes

What can I expect on a flight to Western Massachusetts?
Factors like which carrier you choose and where your plane takes off from will largely determine your experience. You're likely to find all types of flights to Western Massachusetts, from cheap flights for family vacations to first class airfares. Warm meals, entertainment and games for the youngsters are just a little taste of what most airlines offer on long-haul services.

Plane Tickets To Western Massachusetts

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Western Massachusetts. Browse through our inventory to explore a wide range of cheap flights to Western Massachusetts to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Western Massachusetts as you anxiously await to exit the plane and explore what Western Massachusetts has to offer. Considering all the amazing local food and culture in Western Massachusetts, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Western Massachusetts to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Western Massachusetts without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Western Massachusetts with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Western Massachusetts today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.