The Berkshires Vacation Rentals

64 rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in The Berkshires, MA

Book a vacation rental in The Berkshires that has the highest visitor rating. Here are 6 of the best vacation rentals in The Berkshires.
Cozy Berkshire cottage with fireplace.
10

Excellent

·
Apartment
·
3 br
·
Sleeps 5
·
Air Conditioning · Fireplace · Outdoor Space ·
From
$225/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Wifi
Oven
Mountains
Dishwasher
In Unit Laundry
Furnished
Other spaces
Outdoor Space, Kitchen
Central Berkshire Bungalow by Evergreen Home
10

Excellent

·
House
·
2 br
·
Sleeps 5
·
Wifi · Air Conditioning · Outdoor Space ·
From
$196/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Wifi
Air Conditioning
In Unit Laundry
Hardwood Floor
Furnished
Dishwasher
Oven
Other spaces
Outdoor Space, Kitchen, Workspace
Chic Pittsfield Home With A View!
10

Excellent

·
House
·
3 br
·
Sleeps 6
·
Furnished · Mountains · Kitchen ·
From
$227/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Furnished
Mountains
Wifi
Hardwood Floor
Fireplace
Oven
Dishwasher
Beach
Other spaces
Kitchen, Deck, Balcony
Featured in a Home & Garden TV Special 30 South Mountain Road
10

Excellent

·
House
·
2 br
·
Sleeps 4
·
Fireplace · Mountains · Furnished ·
From
$290/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Fireplace
Mountains
Furnished
Oven
Wifi
Air Conditioning
Dishwasher
In Unit Laundry
Other spaces
Kitchen, Outdoor Space
Ski the Berkshires at Beautiful Family Friendly Hygge House
10

Excellent

·
House
·
3 br
·
Sleeps 6
·
Fitness Center · Dishwasher · Air Conditioning ·
From
$405/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
Berkshires Colonial on 2 Acres by Evergreen Home
10

Excellent

·
House
·
4 br
·
Sleeps 10
·
Garage Parking · Wifi · Waterfront ·
From
$375/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Garage Parking
Wifi
Waterfront
Furnished
Oven
Lake
In Unit Laundry
Fireplace
Other spaces
Kitchen, Outdoor Space, Workspace

Our Recommended Vacation Rentals in The Berkshires, MA

We analyzed vacation rentals in The Berkshires 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 The Berkshires to help you find a deal for your next trip.
'The Mill River Cabin’ w/ Fireplace & River View!
9.8

Excellent

·
House
·
2 br
·
Sleeps 5
·
Central Heat · Kitchen · Tv ·
From
$175/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Central Heat
Tv
Air Conditioning
Wifi
Free Parking
Other spaces
Kitchen, Garden
Hilton Garden Inn Lenox Pittsfield
8.6

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Wheelchair Accessible · Free Parking · Workspace ·
From
$175/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

·
Apartment
·
5 br
·
Sleeps 9
·
Air Conditioning · Fireplace · Oven ·
From
$354/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

Budget-Friendly Vacation Rentals in The Berkshires, MA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in The Berkshires 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

·
Apartment
·
2 br
·
Outdoor Space · Balcony ·
From
$42/night
Min stay: 30 nights
Property
Apartment · 2 Beds · 1 bath
Other spaces
Balcony
Large one bedroom

No rating

·
Condo
·
1 br
·
Dishwasher · Assigned Parking · Hardwood Floor ·
From
$53/night
Min stay: 30 nights
Property
Condo · 1 Bed · 1 bath
Amenities
Dishwasher
Assigned Parking
Hardwood Floor
On Site Laundry
Microwave
Garage Parking
Furnished
Carpet
Other spaces
Outdoor Space
Apartment Newly Remodeled Super Location
10

Excellent

·
Apartment
·
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

·
Hotel
·
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

·
Hotel
·
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
CARRIAGE HOUSE | NEW MARLBOROUGH, MA

No rating

·
House
·
2 br
·
Balcony · Hardwood Floor · Assigned Parking ·
From
$107/night
Min stay: 30 nights
Property
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Assigned Parking
Dishwasher
Air Conditioning
Garage Parking
In Unit Laundry
Other spaces
Balcony
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Updated: March 3, 2024