Vacation Rentals in Pittsfield, MA

51 rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Pittsfield, MA

Book a vacation rental in Pittsfield that has the highest visitor rating. Here are 6 of the best vacation rentals in Pittsfield.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
10

Excellent

·
Pittsfield
·
8 br
·
Sleeps 25
·
Dishwasher · Lake · Workspace ·
From
$388/night
Check availability
Property
House · 8 Beds · 3 baths
Amenities
Dishwasher
Lake
Waterfront
Air Conditioning
In Unit Laundry
Residents Lounge
On Site Laundry
Swimming Pool
Other spaces
Workspace, Balcony, Kitchen
Dancing Horse Lodge
10

Excellent

·
Pittsfield
·
3 br
·
Sleeps 6
·
Wifi · Mountains · Outdoor Space ·
From
$135/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Wifi
Mountains
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Outdoor Space, Kitchen
Chic Pittsfield Home With A View!
10

Excellent

·
Pittsfield
·
3 br
·
Sleeps 6
·
Furnished · Mountains · Kitchen ·
From
$252/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Furnished
Mountains
Wifi
Hardwood Floor
Fireplace
Oven
Dishwasher
Beach
Other spaces
Kitchen, Deck, Balcony
Country Living just minutes from Everything! Now offering Seasonal Discounts!
10

Excellent

·
Pittsfield
·
3 br
·
Sleeps 8
·
Outdoor Space · Workspace · Kitchen ·
From
$267/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Wifi
Fitness Center
Fireplace
Furnished
Mountains
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen, Deck
Ski the Berkshires at Beautiful Family Friendly Hygge House
10

Excellent

·
Pittsfield
·
3 br
·
Sleeps 6
·
Fitness Center · Dishwasher · Air Conditioning ·
From
$367/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Mountains
Fireplace
Other spaces
Kitchen, Outdoor Space, Workspace
Spacious Historic Home in the Berkshires!
10

Excellent

·
Pittsfield
·
5 br
·
Sleeps 9
·
Dishwasher · Wifi · Ceiling Fan ·
From
$252/night
Check availability
Property
House · 5 Beds · 2 baths
Amenities
Dishwasher
Wifi
Ceiling Fan
Furnished
Air Conditioning
Central Heat
Oven
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen

Our Recommended Vacation Rentals in Pittsfield, MA

We analyzed vacation rentals in Pittsfield from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Pittsfield to help you find a deal for your next trip.
Hilton Garden Inn Lenox Pittsfield
8.6

Very good

·
Pittsfield
·
1 br
·
Sleeps 4
·
Wheelchair Accessible · Free Parking · Workspace ·
From
$195/night
Check availability
Property
Hotel · 1 Bed
Amenities
Wheelchair Accessible
Free Parking
Wifi
Dry Cleaning Service
Storage
Hot Tub
Pool
Air Conditioning
Other spaces
Workspace
Spacious Historic Home in the Berkshires!

No rating

·
Pittsfield
·
5 br
·
Sleeps 9
·
Air Conditioning · Fireplace · Oven ·
From
$358/night
Check availability
Property
Apartment · 5 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Oven
Furnished
Wifi
Free Parking
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!

No rating

·
Pittsfield
·
3 br
·
Sleeps 10
·
Fireplace · Dishwasher · In Unit Laundry ·
From
$218/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
On Site Laundry
Garage Parking
Furnished
Central Heat
Air Conditioning
Other spaces
Balcony, Kitchen

Budget-Friendly Vacation Rentals in Pittsfield, MA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Pittsfield starting at $42. Use the price filter at the top of the page to search for more specific prices.
15 High St #1

No rating

·
Pittsfield
·
2 br
·
Outdoor Space · Balcony ·
From
$42/night
Min stay: 30 nights
Property
Apartment · 2 Beds · 1 bath
Other spaces
Balcony
$1850/month - Furnished 1 Bedroom In Pittsfield, close to BMC

No rating

·
Pittsfield
·
1 br
·
Furnished · Outdoor Space · Deck ·
From
$62/night
Min stay: 90 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Other spaces
Deck
Apartment Newly Remodeled Super Location
10

Excellent

·
Pittsfield
·
2 br
·
Sleeps 4
·
Oven · Wifi · Balcony ·
From
$75/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
Wifi
Air Conditioning
In Unit Laundry
Hardwood Floor
Furnished
Storage
Other spaces
Balcony, Kitchen
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.3

Very good

·
Pittsfield
·
1 br
·
Sleeps 6
·
Ski In Ski Out · Storage · Furnished ·
From
$91/night
Check availability
Property
Hotel · 1 Bed
Amenities
Ski In Ski Out
Storage
Furnished
On Site Laundry
Swimming Pool
Residents Lounge
Air Conditioning
Wifi
Other spaces
Outdoor Space, Workspace
Best Western Plus Berkshire Hills Inn & Suites
7.8

Very good

·
Pittsfield
·
1 br
·
Sleeps 6
·
Fitness Center · On Site Laundry · Business Center ·
From
$96/night
Check availability
Property
Hotel · 1 Bed
Amenities
Fitness Center
On Site Laundry
Business Center
Wheelchair Accessible
Residents Lounge
Furnished
Elevator
Free Parking
Other spaces
Workspace, Outdoor Space
Traveling Nurses! Paradise, 0.2 Miles from BMC - 3 Bedroom

No rating

·
Pittsfield
·
3 br
·
Sleeps 3
·
Hardwood Floor · Dishwasher · Furnished ·
From
$114/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Hardwood Floor
Dishwasher
Furnished
Oven
Hot Tub
Storage
High Ceilings
On Site Laundry
Other spaces
Outdoor Space, Kitchen
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Updated: February 29, 2024