Rated 5.0 · Best rentals in Berkshire County
Car Rentals in Pittsfield, MA

Rent a brand-new
Toyota in the Berkshires.

5FIFTY5 Rentals makes car rental simple, stylish, and stress-free. Our fleet of brand-new Toyotas is delivered clean, fueled, and ready to go wherever you are in the Berkshires — your door, hotel, or the Albany airport.

View Fleet
Vehicle
Any vehicle
5 options available
Pickup location
Pittsfield, MA
Free delivery in county
5.0★
Google rating
500+
Happy renters
100%
New Toyotas
Free
County delivery
24/7
Text support
About 5FIFTY5

Simple. Stylish.
Stress-free.

At 5FIFTY5, we specialize in providing clean, reliable, and comfortable cars that make every trip stress-free.

Whether you're heading out for a business meeting, a weekend getaway, or just need a dependable vehicle while yours is in the shop, we've got you covered. Our fleet features a range of well-maintained, brand-new Toyotas — from practical sedans to roomy SUVs — all backed by transparent pricing and friendly customer service.

Renting a car with us is simple, fast, and designed around your needs. We deliver to your door, hotel, or the Albany airport anywhere in the Berkshires.

Based in
Pittsfield, MA
Serving
All of Berkshire County
Jurisdiction
Commonwealth of MA
Sister brand
Radical Rentals (boats)
5 vehicles available · 7+ in inventory

The fleet.

Every vehicle in our lineup is a brand-new Toyota chosen for comfort, safety, and reliability. Detailed between rentals. Fueled before pickup.

Toyota HighlanderPREMIUMPearl White
2026 TOYOTA
Highlander
Midsize SUV · 3 Rows
$80
per day
8 seats36 MPGHybrid
Three rows of seating, AWD, Berkshire-ready. Our newest Highlander blends space, comfort, and sophistication — perfect for families, group getaways, or ski gear.
Toyota SiennaCOMING SOONBlack
2026 TOYOTA
Sienna
Minivan · 8 Passengers
Soon
coming soon
8 seats36 MPGHybrid
Premium minivan comfort for group and family travel. Our flagship for multi-generation trips, airport shuttles, and anyone who needs serious seating plus luggage.
Toyota Corolla CrossMagnetic Gray
2026 TOYOTA
Corolla Cross
Crossover
$65
per day
5 seats42 MPGHybrid
Compact yet versatile, built for everyday convenience and spontaneous trips alike. Elevated seating, ample cargo space, and modern features for a relaxed drive.
Toyota RAV4MOST POPULARSilver
2026 TOYOTA
RAV4
Compact SUV
$70
per day
5 seats41 MPGHybrid
Adventure-ready and efficient. Roomy seating, smart safety tech, and excellent fuel economy — ideal for everything from city commutes to weekend getaways.
Toyota CorollaBEST VALUEBlack
2026 TOYOTA
Corolla
Sedan
$65
per day
5 seats50 MPGHybrid
A classic reinvented. Smooth ride, advanced safety, and impressive efficiency in a sleek, easy-to-drive package. Great for commuters, couples, or reliable transport.
Toyota Highlander
SPOTLIGHT · BRAND-NEW 2026
Highlander
3 ROWS · HYBRID
SNOW-RATED AWD
★ FAMILY FAVORITE

Room for everyone,
and all their stuff.

Our newest Highlander blends space, comfort, and sophistication. With three rows of seating, advanced safety features, and a smooth, quiet ride, it's perfect for families, group getaways, or anyone who wants extra room without sacrificing style or efficiency.

8
Passengers
36
MPG combined
3
Rows of seating
AWD
All-wheel drive
View all 5 vehicles
How it works

Rent a car in 4 steps.

STEP 01
Pick your ride
Browse the fleet, choose dates, and tell us where to deliver. 90 seconds on your phone.
STEP 02
Request it
Confirmed within 20 minutes — we send photos of the exact car. Clear pricing, no surprises.
STEP 03
We deliver
Clean, fueled, detailed. Paperwork in four minutes. Keys in hand at your door, hotel, or airport.
STEP 04
Hit the road
Extend anytime. Return to us or we'll pick it up wherever. Berkshires-ready year-round.
Pricing

One rate. No surprises.

Our price is the price. Brand-new Toyotas delivered free in Berkshire County. Extensions are simple — pay the published per-day rate and keep driving.

Compact
Corolla · Corolla Cross
from$65/day
  • Free county delivery
  • Full tank at pickup
  • 50 MPG efficiency
  • Easy extension
MOST POPULAR
SUV
RAV4 · Highlander
from$70/day
  • Everything in Compact
  • Room for 5–8 passengers
  • AWD + snow-rated
  • Priority booking
COMING SOON
Minivan
Sienna — groups & airport shuttles
Soon
  • 8 passengers + luggage
  • Multi-gen trip ready
  • Power sliding doors
  • Airport shuttle capable
Delivery area

All of Berkshire County. Free.

Free delivery anywhere in Berkshire County. We'll also meet you at Albany International ($40), the Hudson train station, or anywhere within a 90-minute drive of Pittsfield.

PittsfieldHQ
Lenox
Williamstown
North Adams
Adams
Lee
Stockbridge
Great Barrington
Sheffield
VERMONTNEW YORKCONNECTICUTNorth AdamsAdamsWilliamstownLenoxLeeStockbridgeGreat BarringtonSheffieldPittsfieldN010 MI
SERVICE AREA
Berkshire County, MA
Policies & Requirements

Know before you go.

Clear policies, no surprises. Submitting a payment through our form is optional — you may also pay in person or by phone after confirming your total.

Payment & Card on File

Do not enter or submit a payment amount until you have confirmed your total due with a 5FIFTY5 representative. A valid card on file is required to cover any additional charges such as toll fees, late returns, or damages.

Tolls & Traffic Violations

Renter is fully responsible for all toll charges, parking fees, penalties, and administrative fees during the rental period. Any tolls or fines billed to 5FIFTY5 after the rental will be charged to the card on file along with related processing fees.

Documentation Required

  • Valid driver's license (front & back)
  • Proof of insurance / registration
  • Credit card in renter's name
  • Must be 25 or older

Legal & Privacy

Massachusetts jurisdiction. Hold harmless waiver covers: Release of Liability, Indemnification, Assumption of Risk, Severability, and Entire Agreement. SMS opt-in for confirmations and reminders — reply STOP to opt out. License/insurance verified against appropriate agencies.

Reviews

Happy renters.

Real feedback from real Berkshires travelers. See us on Google →

"Delivered the RAV4 to our Airbnb in Stockbridge at 8am on a Saturday. Full tank, spotless, brand-new."

Marisa K.
Boston, MA
Rented RAV4

"Flew into Albany, had a Highlander waiting. Paperwork took four minutes. Four."

Derek P.
Brooklyn, NY
Rented Highlander

"The Corolla was spotless and got us everywhere. Best price in the county, hands down."

The Chens
Great Barrington, MA
Rented Corolla
Questions

Frequently asked.

Tell us where — your door, hotel, Airbnb, or Albany airport. We bring the car to you clean, fueled, and ready. No shuttle buses, no counters. County delivery is free; Albany airport is a flat $40.
A valid driver's license (front + back), a credit card in your name, and proof of insurance / registration. You must be 25 or older. That's it.
Yes. Our fleet is 100% brand-new, current-model-year Toyotas. Every vehicle is detailed between rentals and fueled before pickup.
Anytime. Call, text, or fill out the extension form. As long as the car is not booked after you, it is yours. Extension rates are the published per-day rate.
We run year-round. Every vehicle is AWD or hybrid AWD with snow-rated tires from October through April.
A valid card on file is required to cover tolls, late returns, or damages. We can walk you through insurance coverage options when we confirm your booking.
If tolls or fines are billed to 5FIFTY5 after your rental, we charge the card on file for the total plus any related processing fees. You drive, you pay the tolls — straightforward.
Ready to roll

Your next Toyota is ready.

Book online in 90 seconds. Cars can be delivered today if reserved before 2pm.

Or call (413) 822-6208