Cheap Flights to Western Massachusetts from $52

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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 $100 and $52 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Nov 6 - Fri, Nov 13
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Nov 6 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Fri, Nov 13, priced at $100 found 1 day ago
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 2 to September 5$103
RSWWindsor LocksSeptember 15 to September 20$175
JFKWindsor LocksOctober 1 to October 3$227
JFKLathamSeptember 5 to September 11$273
JFKWorcesterSeptember 12 to September 12$313
RSWWorcesterAugust 25 to August 26$368
MANWindsor LocksAugust 27 to August 31$692
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 1 to August 15$352
JFKWindsor LocksAugust 1 to September 2$397
RSWLathamAugust 1 to August 10$487
JFKWorcesterJuly 31 to August 2$593
JFKLathamAugust 1 to August 2$708
MANWindsor LocksJuly 31 to August 30$1,047
*Prices include taxes and fees

Western Massachusetts Flight Information

Traveling to
Western Massachusetts
Lowest Price
$100
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
$68 nightly
The price is $74 total per night from Jul 29 to Jul 30
$74 total
Jul 29 - Jul 30
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 (1,002 reviews)
"If you like cobweb-covered light fixtures, dirt-encrusted carpet, musty stench and ancient unsleepable beds, then this is the motel for you. We booked in here expecting a basic stay, but this was so much less than that. Thick cobwebs looked like Hollywood 'haunted mansion' prop on bathroom lights. ..."

Reviewed on Jul 28, 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
$101 nightly
The price is $115 total per night from Aug 5 to Aug 6
$115 total
Aug 5 - Aug 6
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! (1,007 reviews)
"Had people outside my door until 3:30am being loud not caring."

Reviewed on Jul 27, 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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Opens in a new windowWagon Wheel Inn
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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
$358 nightly
The price is $399 total per night from Aug 9 to Aug 10
$399 total
Aug 9 - Aug 10
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 ...
9.2/10 Wonderful! (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."

Reviewed on Jul 14, 2026

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
$165 nightly
The price is $184 total per night from Aug 3 to Aug 4
$184 total
Aug 3 - Aug 4
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 Massachusetts Museum of Contemporary ...
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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.

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
$134 nightly
The price is $150 total per night from Aug 11 to Aug 12
$150 total
Aug 11 - Aug 12
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! (2,480 reviews)

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

Travelers say...
"This place was awesome!!!! The staff was so nice. The location is beautiful, and it's super easy to drive to fun attractions. I honestly wish I could have stayed longer!"

Reviewed on Jul 27, 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
$119 nightly
The price is $135 total per night from Aug 2 to Aug 3
$135 total
Aug 2 - Aug 3
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! (1,299 reviews)

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

Travelers say...
"Breakfast attendant was awesome"

Reviewed on Jul 27, 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 Aug 9 to Aug 10
$158 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
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
$110 nightly
The price is $125 total per night from Aug 23 to Aug 24
$125 total
Aug 23 - Aug 24
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 Big E and MGM ...
9.4/10 Exceptional! (264 reviews)
"The hotel’s name speaks for itself. It’s a modern, clean, comfortable environment that meets the needs of a quick getaway, business trip, etc. It was reasonably priced. The one drawback is that there are No POOLS !!! Please call ahead to confirm that there is no pool to manage expectations. The room ..."

Reviewed on Jul 27, 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.
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $1,119, price is now $982 per person
$982
per person
Aug 27 - Sep 3
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,828, price is now $1,296 per person
$1,296
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Price was $1,312, price is now $1,141 per person
$1,141
per person
Aug 27 - Sep 3
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Miami to Western Massachusetts
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Western Massachusetts flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
Price was $1,298, price is now $1,234 per person
$1,234
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,394, price is now $1,241 per person
$1,241
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
The White House Inn

The White House Inn

3.5 out of 5
Price was $1,357, price is now $1,275 per person
$1,275
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Dallas 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 $100. 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, November 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. $100 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 $100 and $1,047 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.