Cheap Flights to Western Massachusetts from $39

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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 $102 and $39 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Sep 12 - Fri, Sep 19
TPA
Tampa Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 9 hours ago
$102
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Sep 12 from Tampa Intl. to Bradley Intl., returning Fri, Sep 19, priced at $102 found 9 hours ago

Western Massachusetts Flight Information

Traveling to
Western Massachusetts
Lowest Price
$102
Number of Airlines Serving
Airlines Serving
Breeze Airways
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
The price is $71 per night from May 13 to May 14
$71
includes taxes & fees
$65 per night
May 13 - May 14
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 (964 reviews)
Clean room
"The room and bathroom were very clean."

Reviewed on Jan 3, 2025

Pleasant 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
The price is $107 per night from Jun 1 to Jun 2
$107
includes taxes & fees
$94 per night
Jun 1 - Jun 2
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! (1,001 reviews)
"Very good"

Reviewed on May 3, 2025

Red Roof Inn PLUS+ West Springfield
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is $77 per night from May 10 to May 11
$77
includes taxes & fees
$69 per night
May 10 - May 11
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! (603 reviews)
"Great location. Pleasant staff."

Reviewed on Oct 13, 2024

Wagon 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 ...
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
Lantern 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
The price is $833 per night from May 15 to May 16
$833
includes taxes & fees
$746 per night
May 15 - May 16
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on Jul 27, 2024

The 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
The price is $197 per night from May 26 to May 27
$197
includes taxes & fees
$176 per night
May 26 - May 27
Stay at this 3.5-star historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)
"Location was great, the staff was great, the accommodations were great."

Reviewed on May 2, 2025

Hotel 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 ...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

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The Orchards Hotel
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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 ...
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
Lantern 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
The price is $133 per night from May 11 to May 12
$133
includes taxes & fees
$119 per night
May 11 - May 12
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,802 reviews)

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

Travelers say...
"It was off season and quiet. Great price :)"

Reviewed on May 3, 2025

Vacation 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
The price is $129 per night from May 21 to May 22
$129
includes taxes & fees
$114 per night
May 21 - May 22
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! (1,281 reviews)

Families like: Indoor pool, game room, cribs, rollaway beds

Travelers say...
"👍"

Reviewed on May 4, 2025

La 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
The price is $150 per night from Jun 8 to Jun 9
$150
includes taxes & fees
$134 per night
Jun 8 - Jun 9
Stay at this 3-star 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. ...
9.2/10 Wonderful! (2,296 reviews)

Reviewed on May 5, 2025

D. Hotel Suites & Spa
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Sheraton Springfield Monarch Place Hotel

Sheraton Springfield Monarch Place Hotel

3.5 out of 5
1 Monarch Place, Springfield, MA
The price is $173 per night from May 26 to May 27
$173
includes taxes & fees
$152 per night
May 26 - May 27
Stay at this 3.5-star business-friendly hotel in Springfield. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
7.8/10 Good! (942 reviews)
"The staff was so accommodating!"

Reviewed on Mar 24, 2025

Sheraton Springfield Monarch Place 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.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

2.5 out of 5
per person
Jun 21 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)
Hampton Inn & Suites Albany Airport

Hampton Inn & Suites Albany Airport

2.5 out of 5
per person
Jun 22 - Jun 30
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
per person
Jun 21 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)
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Need a Car For After Your Flight?

Standard

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$37

$99 total
found 4 hours ago
Standard undefined

Midsize

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$38

$101 total
found 4 hours ago
Midsize undefined

Fullsize

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$39

$104 total
found 4 hours ago
Fullsize undefined

Economy

  • 4 people
  • Unlimited mileage
Albany, New York, USA

$39

$105 total
found 4 hours ago
Economy undefined
Lowest prices found within the past 4 hours. Prices and availability subject to change. Additional terms may apply.

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 $102. 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, September 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. $102 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 $102 and $102 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!

*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.