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
TPA
Tampa Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | November 3 to November 10 | $97 |
| RSW | Latham | November 4 to November 11 | $127 |
| RSW | Windsor Locks | December 4 to December 8 | $150 |
| RSW | Worcester | November 14 to November 17 | $183 |
| JFK | Latham | December 11 to December 17 | $237 |
| JFK | Worcester | December 10 to December 12 | $308 |
| MAN | Windsor Locks | November 24 to December 1 | $663 |
| MAN | Latham | November 6 to November 9 | $1,015 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | November 1 to November 10 | $99 |
| RSW | Windsor Locks | November 1 to November 5 | $195 |
| JFK | Latham | November 1 to November 4 | $360 |
| RSW | Latham | November 2 to November 3 | $495 |
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
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
Red Roof Inn PLUS+ West Springfield
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
Wagon Wheel Inn
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
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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
$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
Hotel Northampton
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
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
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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
$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
La Quinta Inn & Suites by Wyndham Springfield MA
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
D. Hotel Suites & Spa
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
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
$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
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.
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Frequently asked questions
Plane Tickets To Western Massachusetts
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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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