Cheap Flights to Western Massachusetts from $35

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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 $97 and $35 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
JFKWindsor LocksNovember 3 to November 10$97
RSWLathamNovember 4 to November 11$127
RSWWindsor LocksDecember 4 to December 8$150
RSWWorcesterNovember 14 to November 17$183
JFKLathamDecember 11 to December 17$237
JFKWorcesterDecember 10 to December 12$308
MANWindsor LocksNovember 24 to December 1$663
MANLathamNovember 6 to November 9$1,015
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksNovember 1 to November 10$99
RSWWindsor LocksNovember 1 to November 5$195
JFKLathamNovember 1 to November 4$360
RSWLathamNovember 2 to November 3$495
*Prices include taxes and fees

Western Massachusetts Flight Information

Traveling to
Western Massachusetts
Lowest Price
$97
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Southwest Airlines
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
$59 nightly
The price is $65 total per night from Nov 1 to Nov 2
$65 total
Nov 1 - Nov 2
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 ...
6.6/10 (1,000 reviews)
Easy to park and check in. Walk up window for motel guest check in. The woman was friendly and got us an extra pillow and came to our room to make sure we had heat. The room was out dated, bathroom clean. I felt like I was sleeping in my grandmother's basement. Has a comfortable bed. A little more ...

Reviewed on Oct 13, 2025

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
$98 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
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 ...
6.8/10 (1,016 reviews)
The staff was very helpful and nice

Reviewed on Oct 12, 2025

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

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Oct 26 to Oct 27
$77 total
Oct 26 - Oct 27
Total with taxes and fees
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! (636 reviews)
Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon.

Reviewed on Oct 17, 2025

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 ...
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

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
$335 nightly
The price is $374 total per night from Nov 9 to Nov 10
$374 total
Nov 9 - Nov 10
Total with taxes and fees
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 ...
9.2/10 Wonderful! (83 reviews)
My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ...

Reviewed on Oct 12, 2025

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
$999 nightly
The price is $1,116 total per night from Oct 26 to Oct 27
$1,116 total
Oct 26 - Oct 27
Total with taxes and fees
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! (1,000 reviews)
Best place around, I would definitely recommend to anyone.

Reviewed on Oct 20, 2025

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

Reviewed on Mar 9, 2020

Opens in a new windowThe 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

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
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,095 reviews)

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

Travelers say...
Room could use some upgrades but then they would just charge more. But the pool and hot tub makes it worth staying.

Reviewed on Oct 22, 2025

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
$115 nightly
The price is $130 total per night from Nov 9 to Nov 10
$130 total
Nov 9 - Nov 10
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! (1,306 reviews)

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

Travelers say...
The property needs work and lots upgrading. The staff was friendly, except for a female manager at the from desk. The female bartender was a delight. Parking was plenty and well lit.

Reviewed on Oct 20, 2025

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 $159 total per night from Oct 26 to Oct 27
$159 total
Oct 26 - Oct 27
Total with taxes and fees
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! (2,253 reviews)
Front desk staff was welcoming and helpful.

Reviewed on Oct 19, 2025

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
$122 nightly
The price is $140 total per night from Nov 23 to Nov 24
$140 total
Nov 23 - Nov 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 Eastern ...
9.2/10 Wonderful! (56 reviews)
Wonderful staff and beautiful new, clean rooms!

Reviewed on Oct 21, 2025

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.
Hilton Garden Inn Albany Airport
The Century House, an Ascend Collection Hotel
Marriott Albany
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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 $97. 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, December 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. $97 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 $97 and $1,015 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.