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 $68 and $35 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply
MCO
Orlando Intl.
BDL
Bradley Intl.
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RSW | Windsor Locks | January 13 to January 14 | $119 |
| RSW | Latham | January 17 to January 24 | $122 |
| JFK | Windsor Locks | January 21 to January 26 | $130 |
| RSW | Worcester | January 15 to January 25 | $166 |
| JFK | Latham | January 23 to January 31 | $246 |
| JFK | Worcester | December 17 to December 23 | $423 |
| MAN | Windsor Locks | March 12 to March 18 | $856 |
| MAN | Latham | February 1 to February 7 | $1,067 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | December 12 to December 16 | $129 |
| RSW | Worcester | December 12 to December 15 | $148 |
| RSW | Windsor Locks | December 13 to December 14 | $255 |
| JFK | Worcester | December 14 to December 16 | $436 |
| JFK | Latham | December 14 to December 16 | $568 |
| RSW | Latham | December 14 to December 18 | $675 |
Western Massachusetts Flight Information
Traveling to | Western Massachusetts |
|---|---|
Lowest Price | $68 |
Number of Airlines Serving | |
Airlines Serving | Frontier 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
42 Stockbridge Rd West Stockbridge MA
$52 nightly
The price is $58 total per night from Jan 1 to Jan 2
$58 total
Jan 1 - Jan 2, 2026
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)
Quite , clean , very good all around.
Reviewed on Dec 2, 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
$85 nightly
The price is $97 total per night from Dec 16 to Dec 17
$97 total
Dec 16 - Dec 17
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 (1,002 reviews)
Nice place
Reviewed on Nov 29, 2025
Wagon Wheel Inn
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 Guido's ...
7/10 Good! (641 reviews)
Good overall.
Reviewed on Oct 26, 2025
Save an average of 15% on thousands of hotels when you're signed in
Lantern House Motel
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
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
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night from Jan 5 to Jan 6
$462 total
Jan 5 - Jan 6, 2026
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 Chesterwood and Norman Rockwell Museum ...
9.2/10 Wonderful! (85 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
Hotel Northampton
36 King Street Northampton MA
$165 nightly
The price is $184 total per night from Dec 11 to Dec 12
$184 total
Dec 11 - Dec 12
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 ...
9/10 Wonderful! (1,000 reviews)
We liked everything!
Reviewed on Nov 29, 2025
The Orchards Hotel
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
Save an average of 15% on thousands of hotels when you're signed in
Lantern House Motel
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
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
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Dec 14 to Dec 15
$141 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this 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! (2,166 reviews)
Families like: Kids pool, playground, game room, skiing nearby
Travelers say...
Clean spacious toom
Reviewed on Dec 6, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street Springfield MA
$111 nightly
The price is $125 total per night from Dec 14 to Dec 15
$125 total
Dec 14 - Dec 15
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! (1,307 reviews)
Families like: Indoor pool, game room, cribs, free breakfast for the whole family
Travelers say...
The staff was amazing and so helpful. They answered all questions and even when i got there at 930 pm they greeted us so cheerfully! In the morning my key card wasnt working for the gym and they came up and opened it for me
Reviewed on Dec 7, 2025
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$121 nightly
The price is $135 total per night from Dec 11 to Dec 12
$135 total
Dec 11 - Dec 12
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. ...
9.2/10 Wonderful! (2,231 reviews)
The check in staff was excellent. Extremely polite and welcoming. Excellent hotel with a very good restaurant attached.
Reviewed on Dec 6, 2025
Save an average of 15% on thousands of hotels when you're signed in
Blue – A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
$111 nightly
The price is $128 total per night from Dec 30 to Dec 31
$128 total
Dec 30 - Dec 31
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 ...
9.4/10 Exceptional! (102 reviews)
Well maintained hotel with a friendly staff. I was very surprised how clean and quiet the hotel was. Book this place! I’ll definitely stay here again when in the area.
Reviewed on Dec 9, 2025
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.
Don't see what you're looking for?
See all available trips from Dallas to Western Massachusetts
View all tripsNeed a Car For After Your Flight?
Midsize
Albany, New York, USA
$40
$107 total
found 22 hours ago
Economy
Albany, New York, USA
$40
$107 total
found 22 hours ago
Compact
Albany, New York, USA
$40
$107 total
found 22 hours ago
Standard
Albany, New York, USA
$41
$119 total
found 22 hours ago
Lowest prices found within the past 22 hours. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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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