Vacation Rentals in Pittsfield, MA
PRICE PER NIGHT
ACCOMMODATION TYPES
Charming Historic Home Close to Downtown and Skiing!
No reviews
·
Pittsfield
·
5 br
·
Sleeps 10
·
Free Parking · Fireplace · Outdoor Space ·
From
$598/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Free Parking
Fireplace
Dishwasher
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Kitchen
Hilton Garden Inn Lenox Pittsfield
8.5
Very good
·
Pittsfield
·
1 br
·
Sleeps 4
·
Pool · Free Parking · On Site Laundry ·
From
$187/nightProperty
Hotel · 1 Bed
Amenities
Pool
Free Parking
On Site Laundry
Fireplace
Air Conditioning
Furnished
Wifi
Fitness Center
Other spaces
Workspace
Ski Jiminy, Hot Tub, Large Open Great Room, Lake View
No reviews
·
Pittsfield
·
4 br
·
Sleeps 10
·
Ceiling Fan · Hot Tub · Fitness Center ·
From
$521/nightProperty
House · 4 Beds · 2 baths
Amenities
Ceiling Fan
Hot Tub
Fitness Center
Free Parking
Lake
Waterfront
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Berkshire Home
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 8
·
Hot Tub · Pool · Outdoor Space ·
From
$369/nightProperty
House · 3 Beds · 1 bath
Amenities
Hot Tub
Pool
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Apartment Newly Remodeled Super Location
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Hardwood Floor · Balcony · Outdoor Space ·
From
$85/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Hardwood Floor
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Balcony, Kitchen
Charming Historic Home Close to Downtown & Skiing!
9.9
Excellent
·
Pittsfield
·
5 br
·
Sleeps 10
·
Toiletries · Garden · Walk In Closets ·
From
$290/nightProperty
House · 5 Beds · 4 baths
Amenities
Toiletries
Walk In Closets
Tv
Microwave
Assigned Parking
Central Heat
Free Parking
Fireplace
Other spaces
Garden, Kitchen
Central Berkshire Bungalow, Long Term Availability
10
Excellent
·
Pittsfield
·
2 br
·
Sleeps 5
·
Hardwood Floor · Ski In Ski Out · Dishwasher ·
From
$185/nightProperty
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Ski In Ski Out
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Chic Pittsfield Home With A View!
No reviews
·
Pittsfield
·
3 br
·
Sleeps 6
·
Beach · Deck · Hardwood Floor ·
From
$266/nightProperty
House · 3 Beds · 2 baths
Amenities
Beach
Hardwood Floor
Mountains
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Other spaces
Deck, Balcony, Kitchen
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Richmond Pond Beauty
9.5
Excellent
·
Pittsfield
·
3 br
·
Sleeps 7
·
Central Heat · Ski In Ski Out · Lake ·
From
$426/nightProperty
House · 3 Beds · 2 baths
Amenities
Central Heat
Ski In Ski Out
Lake
Waterfront
Mountains
Fireplace
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
9.8
Excellent
·
Pittsfield
·
4 br
·
Sleeps 10
·
Ski In Ski Out · Lake · Waterfront ·
From
$679/nightProperty
House · 4 Beds · 4 baths
Amenities
Ski In Ski Out
Lake
Waterfront
Mountains
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Other spaces
Balcony, Kitchen
Beautiful Waterfront home with deep water dock on Onota Lake
9.5
Excellent
·
Pittsfield
·
3 br
·
Sleeps 10
·
Lake · Waterfront · Fireplace ·
From
$257/nightProperty
House · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
Modern 4 bedroom lakefront house in The Berkshires.
10
Excellent
·
Pittsfield
·
4 br
·
Sleeps 8
·
Fitness Center · Lake · Waterfront ·
From
$495/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Lake
Waterfront
Mountains
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Other spaces
Balcony, Kitchen
Lovely Family Retreat in the ♥️ of the Berkshires!
10
Excellent
·
Pittsfield
·
4 br
·
Sleeps 7
·
Workspace · Outdoor Space · Dishwasher ·
From
$349/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Charming Apartment In Berkshire Victorian Home
No reviews
·
Pittsfield
·
3 br
·
Sleeps 8
·
Balcony · Mountains · Workspace ·
From
$287/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Mountains
Dishwasher
Oven
Air Conditioning
Furnished
Wifi
Roof Deck
Other spaces
Balcony, Workspace, Kitchen
Beautiful Home away from Home
8
Very good
·
Pittsfield
·
5 br
·
Sleeps 10
·
Workspace · Fireplace · Outdoor Space ·
From
$160/nightProperty
House · 5 Beds · 3 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
Tranquil Lake House Getaway on Onota Lake
9.9
Excellent
·
Pittsfield
·
5 br
·
Sleeps 10
·
Beach · Ski In Ski Out · Lake ·
From
$557/nightProperty
House · 5 Beds · 2 baths
Amenities
Beach
Ski In Ski Out
Lake
Waterfront
Fireplace
Dishwasher
In Unit Laundry
Oven
Other spaces
Balcony, Kitchen
Winter in the Berkshires at Family Friendly Hygge House
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 6
·
Fitness Center · On Site Laundry · Lake ·
From
$405/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
On Site Laundry
Lake
Waterfront
Mountains
Fireplace
Dishwasher
In Unit Laundry
Other spaces
Workspace, Kitchen
Historical Colonial Near Down Town
No reviews
·
Pittsfield
·
1 br
·
Sleeps 2
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$199/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Beautiful, Newly Renovated Apartment in a Great Location
No reviews
·
Pittsfield
·
1 br
·
Sleeps 2
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$199/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Best Western Plus Berkshire Hills Inn & Suites
7.7
Very good
·
Pittsfield
·
1 br
·
Sleeps 6
·
Smoking Allowed · Carpet · Free Parking ·
From
$93/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Carpet
Free Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Fitness Center
Other spaces
Workspace
Berkshire Yankee Suites - An Extended Stay Hotel
9.2
Excellent
·
Pittsfield
·
1 br
·
Sleeps 4
·
Carpet · Assigned Parking · Free Parking ·
From
$188/nightProperty
Hotel · 1 Bed · 1 bath
Amenities
Carpet
Assigned Parking
Free Parking
On Site Laundry
Dishwasher
Oven
Air Conditioning
Furnished
Other spaces
Balcony, Workspace, Kitchen
Hotel on North
9
Excellent
·
Pittsfield
·
1 br
·
Sleeps 4
·
Assigned Parking · Free Parking · On Site Laundry ·
From
$116/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Free Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Storage
Business Center
Other spaces
Workspace
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.6
Very good
·
Pittsfield
·
1 br
·
Sleeps 6
·
Smoking Allowed · Carpet · Pool ·
From
$91/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Carpet
Pool
Ski In Ski Out
On Site Laundry
Mountains
Air Conditioning
Furnished
Other spaces
Workspace
Lovely ranch home getaway in Berkshire County
9.9
Excellent
·
Pittsfield
·
2 br
·
Sleeps 4
·
Deck · On Site Laundry · Lake ·
From
$300/nightProperty
House · 2 Beds · 2 baths
Amenities
On Site Laundry
Lake
Waterfront
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Other spaces
Deck, Kitchen
Grand Colonial Home in the Heart of The Berkshires
9.9
Excellent
·
Pittsfield
·
4 br
·
Sleeps 12
·
Deck · Outdoor Space · Dishwasher ·
From
$419/nightProperty
House · 4 Beds · 3 baths
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Deck, Kitchen
Condo Resort in Cultural Art Haven, Berkshire
No reviews
·
Pittsfield
·
1 br
·
Sleeps 4
·
Hot Tub · Pool · On Site Laundry ·
From
$654/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Hot Tub
Pool
On Site Laundry
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
SAFE AND COZY BERKSHIRES GETAWAY
9.9
Excellent
·
Pittsfield
·
3 br
·
Sleeps 6
·
Lake · Waterfront · Mountains ·
From
$230/nightProperty
House · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Mountains
Dishwasher
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Kitchen
Cozy Berkshire cottage with fireplace.
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 5
·
Free Parking · Mountains · Fireplace ·
From
$251/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Free Parking
Mountains
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
Hidden Oasis in the Berkshire Mountains
10
Excellent
·
Pittsfield
·
5 br
·
Hot Tub · Mountains · Fireplace ·
From
$498/nightProperty
House · 5 Beds · 3 baths
Amenities
Hot Tub
Mountains
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
Charming Historic Home Close to Downtown & Skiing!
9.8
Excellent
·
Pittsfield
·
5 br
·
Sleeps 10
·
Central Heat · Fireplace · Outdoor Space ·
From
$409/nightProperty
House · 5 Beds · 4 baths
Amenities
Central Heat
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.6
Excellent
·
Pittsfield
·
8 br
·
Ceiling Fan · Assigned Parking · Central Heat ·
From
$375/nightProperty
House · 8 Beds · 3 baths
Amenities
Ceiling Fan
Assigned Parking
Central Heat
Fitness Center
On Site Laundry
Fireplace
Dishwasher
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Lakeside Home With Pool-Completely Renovated
10
Excellent
·
Pittsfield
·
6 br
·
Sleeps 16
·
Pool · Fireplace · Outdoor Space ·
From
$700/nightProperty
House · 6 Beds · 5 baths
Amenities
Pool
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Dancing Horse Lodge
9.3
Excellent
·
Pittsfield
·
3 br
·
Sleeps 6
·
In Unit Laundry · Kitchen · Oven ·
From
$132/nightProperty
House · 3 Beds · 1 bath
Amenities
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Honeysuckle Rose Cottage
8.9
Very good
·
Pittsfield
·
2 br
·
Sleeps 4
·
In Unit Laundry · Kitchen · Oven ·
From
$118/nightProperty
House · 2 Beds · 1 bath
Amenities
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Ski the Berkshires!
10
Excellent
·
Pittsfield
·
3 br
·
Sleeps 10
·
Deck · Fitness Center · Workspace ·
From
$300/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Deck, Workspace, Kitchen
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
9.5
Excellent
·
Pittsfield
·
3 br
·
Sleeps 7
·
Hardwood Floor · Fitness Center · Workspace ·
From
$288/nightProperty
House · 3 Beds · 3 baths
Amenities
Hardwood Floor
Fitness Center
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Featured in a Home & Garden TV Special 30 South Mountain Road
9.6
Excellent
·
Pittsfield
·
1 br
·
Sleeps 4
·
Mountains · Fireplace · Outdoor Space ·
From
$260/nightProperty
House · 1 Bed · 1 bath
Amenities
Mountains
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Showing 1 - 37 of 37 results
Updated: March 31, 2023
Learn about vacation rentals in
Pittsfield
Explore 37 vacation rentals near Pittsfield, Massachusetts. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Pittsfield, you can see photos of Pittsfield vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Pittsfield vacation rentals in specific areas. Whether you’re looking for a Pittsfield staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Pittsfield is $85 per night and the highest price is $700 per night.
5 of the vacation rentals near Pittsfield are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $199 per night. There are
currently 3 vacation units under this
price. 26 of the vacation rentals near Pittsfield are houses.
The average bathroom count for a vacation house near Pittsfield is
3. The average price for vacation houses near Pittsfield is $369 per night. There are 14 vacation homes under this price. The most common
amenities for vacation rentals near Pittsfield are: furnished, wifi, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
9 available
2 bed rentals
4 available
3 bed rentals
11 available
4+ bed rentals
13 available
Which price range for vacation rentals is considered a good deal in Pittsfield, MA area?
Vacation Rental Price Information in Pittsfield, MA
The graph shows the percentages of vacation homes in each price bucket. Pittsfield, MA has the largest percentage (17.31%) of homes in $100 - $150 price range.
$0 - $50
5
units
$50 - $100
4
units
$100 - $150
9
units
$150 - $200
3
units
$200 - $250
8
units
$250 - $300
5
units
$300 - $350
2
units
$350 - $400
6
units
$400 - $450
4
units
$500+
6
units
Vacation Rentals in Pittsfield, MA FAQ
How many vacation rentals in Pittsfield are available?
There are currently 37 vacation rentals in Pittsfield available. Our vacation rentals in Pittsfield include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Pittsfield?
Yes, right now there are 14 pet friendly vacation rentals in Pittsfield. A pet friendly vacation rental in Pittsfield means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Pittsfield with a pool?
Yes there are vacation rentals with a pool available in Pittsfield, MA. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Pittsfield with internet access?
As of March 31, 2023, there are vacation rentals with internet access available in Pittsfield, Massachusetts. Check out more enjoyable destinations on Vacations by Zumper.
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