Vacation Rentals in Pittsfield, MA
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.
Lovely Family Retreat in the ♥️ of the Berkshires!
10
Excellent
·
Pittsfield
·
4 br
·
Sleeps 7
·
Workspace · Dishwasher · Air Conditioning ·
From
$361/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Workspace, Kitchen
Price drop
Charming Apartment In Berkshire Victorian Home
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 8
·
Mountains · Oven · Wifi ·
From
$249/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Mountains
Oven
Wifi
Air Conditioning
Furnished
Roof Deck
Dishwasher
Other spaces
Workspace, Balcony, Kitchen
Price drop
Stylish cottage located by Pontoosuc Lake with lake views!
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Furnished · Outdoor Space · Residents Lounge ·
From
$299/nightProperty
House · 2 Beds · 2 baths
Amenities
Furnished
Residents Lounge
Air Conditioning
On Site Laundry
Oven
Wifi
Dishwasher
Other spaces
Kitchen, Workspace
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 5
·
Dishwasher · Fitness Center · Outdoor Space ·
From
$209/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
Fitness Center
Air Conditioning
Wifi
Furnished
Oven
On Site Laundry
Other spaces
Kitchen
Country Living just minutes from everything!
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 8
·
Outdoor Space · Workspace · Kitchen ·
From
$317/nightProperty
House · 3 Beds · 2 baths
Amenities
Wifi
Air Conditioning
Fitness Center
Furnished
Oven
Mountains
Dishwasher
On Site Laundry
Other spaces
Workspace, Kitchen, Deck
Price drop
Summer in the Berkshires at Family Friendly Hygge House
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 6
·
Air Conditioning · Fireplace · Waterfront ·
From
$416/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Waterfront
Furnished
Oven
Mountains
Fitness Center
Dishwasher
Other spaces
Kitchen, Workspace
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.
Downtown Pittsfield Vacation Rental Near Hiking!
No rating
·
Pittsfield
·
2 br
·
Sleeps 7
·
Workspace · Wifi · Kitchen ·
From
$216/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Wifi
Oven
In Unit Laundry
Furnished
Dishwasher
Air Conditioning
Other spaces
Workspace, Kitchen
Price drop
Hilton Garden Inn Lenox Pittsfield
8.6
Very good
·
Pittsfield
·
1 br
·
Sleeps 4
·
Workspace · Air Conditioning · Wifi ·
From
$180/nightProperty
Hotel · 1 Bed
Amenities
Air Conditioning
Wifi
Wheelchair Accessible
Free Parking
Business Center
Pool
Storage
Fitness Center
Other spaces
Workspace
Spacious Historic Home in the Berkshires!
No rating
·
Pittsfield
·
5 br
·
Sleeps 9
·
Air Conditioning · Fireplace · Oven ·
From
$597/nightProperty
Apartment · 5 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Oven
Furnished
Wifi
Free Parking
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Downtown Pittsfield Vacation Rental Near Hiking!
No rating
·
Pittsfield
·
2 br
·
Sleeps 7
·
Kitchen · Free Parking · Furnished ·
From
$441/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Free Parking
Furnished
Wifi
Oven
Dishwasher
Air Conditioning
Other spaces
Kitchen, Workspace
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 $78. Use the price filter at the top of the page to search for more specific prices.
Apartment Newly Remodeled Super Location
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Oven · Wifi · Air Conditioning ·
From
$78/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
Wifi
Air Conditioning
On Site Laundry
Furnished
Hardwood Floor
Storage
Other spaces
Kitchen, Balcony
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.4
Very good
·
Pittsfield
·
1 br
·
Sleeps 6
·
Ski In Ski Out · Storage · Furnished ·
From
$91/nightProperty
Hotel · 1 Bed
Amenities
Ski In Ski Out
Storage
Furnished
On Site Laundry
Swimming Pool
Residents Lounge
Air Conditioning
Wifi
Other spaces
Workspace
Best Western Plus Berkshire Hills Inn & Suites
7.7
Very good
·
Pittsfield
·
1 br
·
Sleeps 6
·
Fitness Center · On Site Laundry · Business Center ·
From
$96/nightProperty
Hotel · 1 Bed
Amenities
Fitness Center
On Site Laundry
Business Center
Wheelchair Accessible
Residents Lounge
Furnished
Elevator
Free Parking
Other spaces
Workspace
Price drop
2/BR Historic District-Long Term Rentals Welcome!
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Oven · Dishwasher · Kitchen ·
From
$101/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
Dishwasher
In Unit Laundry
Furnished
Swimming Pool
Wifi
Air Conditioning
Other spaces
Kitchen
2/BR Historic District Apartment
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Air Conditioning · Swimming Pool · In Unit Laundry ·
From
$111/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
Swimming Pool
In Unit Laundry
Furnished
Oven
Wifi
Other spaces
Kitchen
Traveling Nurses! Paradise, 0.2 Miles from BMC - 3 Bedroom
No rating
·
Pittsfield
·
3 br
·
Sleeps 3
·
Hardwood Floor · Dishwasher · Furnished ·
From
$114/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Hardwood Floor
Dishwasher
Furnished
Oven
Hot Tub
Storage
High Ceilings
On Site Laundry
Other spaces
Kitchen
Vacation Rentals With AC and/or Heat in Pittsfield, MA
Whether you need air conditioning or central heating, these vacation rentals are for you.
Price drop
Spacious Historic Home in the Berkshires!
No rating
·
Pittsfield
·
5 br
·
Sleeps 9
·
Fireplace · Wifi · Air Conditioning ·
From
$312/nightProperty
House · 5 Beds · 2 baths
Amenities
Fireplace
Wifi
Air Conditioning
On Site Laundry
Furnished
Dishwasher
Oven
Central Heat
Other spaces
Balcony, Workspace, Kitchen
Price drop
Charming Historic Home Close to Downtown & Skiing!
10
Excellent
·
Pittsfield
·
5 br
·
Sleeps 10
·
Fireplace · Dishwasher · Workspace ·
From
$371/nightProperty
House · 5 Beds · 4 baths
Amenities
Fireplace
Dishwasher
Air Conditioning
Furnished
Oven
In Unit Laundry
Garage Parking
Residents Lounge
Other spaces
Workspace, Kitchen
Charming Historic Home Close to Downtown & Skiing!
9.9
Excellent
·
Pittsfield
·
5 br
·
Sleeps 10
·
Free Parking · Garden · Residents Lounge ·
From
$290/nightProperty
House · 5 Beds · 4 baths
Amenities
Free Parking
Residents Lounge
Assigned Parking
Microwave
Oven
Walk In Closets
Fireplace
Swimming Pool
Other spaces
Garden, Workspace, Kitchen
Expand your search criteria to see more vacation rentals near Pittsfield.
Updated: September 28, 2023
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