Cheap flights from RSW to PSF (Southwest Florida Intl. to Pittsfield Municipal)

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Hotel Ideas near Pittsfield Municipal

Airport Hotels near Pittsfield Municipal

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night from Aug 13 to Aug 14
$173 total
Aug 13 - Aug 14
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,003 reviews)
"Rooms clean, bed comfortable, staff friendly, price reasonable. What more can you ask for?"

Reviewed on Jul 14, 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$156 nightly
The price is $174 total per night from Jul 22 to Jul 23
$174 total
Jul 22 - Jul 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,014 reviews)
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Reviewed on Jul 12, 2026

The Yankee Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
$118 nightly
The price is $132 total per night from Jul 28 to Jul 29
$132 total
Jul 28 - Jul 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,007 reviews)
"Breakfast was meager"

Reviewed on Jul 11, 2026

Best Western Plus Berkshire Hills Inn & Suites
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.

Hotels In Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night from Aug 13 to Aug 14
$173 total
Aug 13 - Aug 14
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,003 reviews)
"Rooms clean, bed comfortable, staff friendly, price reasonable. What more can you ask for?"

Reviewed on Jul 14, 2026

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$63 nightly
The price is $70 total per night from Aug 2 to Aug 3
$70 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.4/10 (852 reviews)
"This hotel presents actual and serious health hazards. As we tried to follow the unhelpful directions to room 230 offered by an impatient clerk, we approached a crumbling cement stairwell where a huge pile of vomit was gathering flies. A foot away, a broken shopping cart filled with garbage, including ..."

Reviewed on Jul 11, 2026

FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
$141 nightly
The price is $157 total per night from Jul 19 to Jul 20
$157 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (133 reviews)
"Very nice and clean hotel for an overnight stay passing through Massachusetts. Located off a very busy road so pulling out of the parking lot can be difficult."

Reviewed on Jul 13, 2026

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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.

Low Priced Pittsfield Hotels

Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St Pittsfield MA
$90 nightly
The price is $101 total per night from Jul 15 to Jul 16
$101 total
Jul 15 - Jul 16
Total with taxes and fees
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (880 reviews)
"clean room. Nice pool."

Reviewed on Jul 14, 2026

Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
$118 nightly
The price is $132 total per night from Jul 28 to Jul 29
$132 total
Jul 28 - Jul 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,007 reviews)
"Breakfast was meager"

Reviewed on Jul 11, 2026

Best Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$79 nightly
The price is $88 total per night from Jul 26 to Jul 27
$88 total
Jul 26 - Jul 27
Total with taxes and fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
8.6/10 Excellent! (379 reviews)
"The space was very nice and very clean. No issues there. However, I reserved for three adults and there were no linens for the sofa bed. Thankfully, our daughter had blankets in her car. When we went to the registration area, no one was on site. (This property is accessed via codes that come in a ..."

Reviewed on Jul 11, 2026

The Central Downtown Inn & Suites
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 Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
$249 nightly
The price is $278 total per night from Jul 15 to Jul 16
$278 total
Jul 15 - Jul 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (874 reviews)
"Wonderful hotel full of character and incredibly kind staff!"

Reviewed on Jul 14, 2026

Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
$118 nightly
The price is $132 total per night from Jul 28 to Jul 29
$132 total
Jul 28 - Jul 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,007 reviews)
"Breakfast was meager"

Reviewed on Jul 11, 2026

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
$130 nightly
The price is $145 total per night from Jul 19 to Jul 20
$145 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,016 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of ..."

Reviewed on Jul 14, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

RSW to PSF Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
RSW Address & GPS
Address:
11000 Terminal Access Road
Fort Myers FL,
United States
IATA Code:
RSW
Longitude:
-81.755263
Latitude:
26.527887
Time Zone:
America/New_York
PSF Address & GPS
Address:
Pittsfield MA,
United States
IATA Code:
PSF
Longitude:
-73.291667
Latitude:
42.426667
Time Zone:
America/New_York

Frequently asked questions

What airlines have the most flights from RSW to PSF?
Do a bit of shopping, grab a coffee, go for a short wander .... Airport stopovers aren't all that bad! If you're traveling between Fort Myers and Pittsfield, you can't fly direct. Be prepared to make at least one stop somewhere.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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