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Vacations by Zumper

The Berkshires Vacation 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 Great Barrington Home ~ 1 Mi to Ski Resort!
10

Excellent

·
House
·
4 br
·
Sleeps 9
·
Assigned Parking · Microwave · Tv ·
From
$224/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Assigned Parking
Microwave
Tv
Oven
Air Conditioning
On Site Laundry
Dishwasher
Central Heat
Other spaces
Kitchen, Garden
Price drop
Cozy Stockbridge Cabin - Walk to Beach & Lake!
10

Excellent

·
House
·
2 br
·
Sleeps 4
·
Residents Lounge · Oven · Dishwasher ·
From
$289/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Residents Lounge
Oven
Dishwasher
Air Conditioning
Tv
Assigned Parking
Lake
Wifi
Other spaces
Kitchen
Restored 1800s Home Half Mile to Ski Resort!
10

Excellent

·
House
·
4 br
·
Sleeps 8
·
Fitness Center · Central Heat · On Site Laundry ·
From
$175/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Fitness Center
Central Heat
On Site Laundry
Toiletries
Air Conditioning
Assigned Parking
Tv
Fireplace
Other spaces
Kitchen, Garden, Workspace
Price drop
Updated Canaan Farmhouse: Pond & Sunset Views!
10

Excellent

·
House
·
3 br
·
Sleeps 6
·
Lake · Assigned Parking · Wifi ·
From
$280/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Lake
Assigned Parking
Wifi
Residents Lounge
Dishwasher
On Site Laundry
Central Heat
Oven
Other spaces
Kitchen
Price drop
Cozy Great Barrington Home about 1 Mi to Ski Resort!
8.5

Very good

·
Apartment
·
4 br
·
Sleeps 9
·
Furnished · Kitchen · Oven ·
From
$525/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Furnished
Oven
Assigned Parking
On Site Laundry
Wifi
Dishwasher
Air Conditioning
Other spaces
Kitchen
Price drop
The Yankee, Trademark Collection by Wyndham
8.3

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Residents Lounge · Furnished · Assigned Parking ·
From
$185/night
Check availability
Property
Hotel · 1 Bed
Amenities
Residents Lounge
Furnished
Assigned Parking
Ski In Ski Out
Fitness Center
Wifi
Smoking Allowed
On Site Laundry
Other spaces
Workspace

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 $55. Use the price filter at the top of the page to search for more specific prices.
Howard Johnson by Wyndham Lenox
6.8

Good

·
Hotel
·
1 br
·
Sleeps 4
·
On Site Laundry · Air Conditioning · Wifi ·
From
$55/night
Check availability
Property
Hotel · 1 Bed
Amenities
On Site Laundry
Air Conditioning
Wifi
Ski In Ski Out
Furnished
Free Parking
Pool
Swimming Pool
Other spaces
Workspace
Quality Inn
8.2

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Furnished · Ski In Ski Out · Free Parking ·
From
$67/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Ski In Ski Out
Free Parking
On Site Laundry
Wifi
Smoking Allowed
Air Conditioning
Holiday Inn Express Great Barrington, an IHG Hotel
8.2

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Assigned Parking · Residents Lounge · Garage Parking ·
From
$76/night
Check availability
Property
Hotel · 1 Bed
Amenities
Assigned Parking
Residents Lounge
Garage Parking
Smoking Allowed
Wifi
Wheelchair Accessible
Pool
Fitness Center
Other spaces
Workspace, Kitchen
Apartment Newly Remodeled Super Location
10

Excellent

·
Apartment
·
2 br
·
Sleeps 4
·
Oven · Wifi · Air Conditioning ·
From
$78/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
Wifi
Air Conditioning
On Site Laundry
Furnished
Hardwood Floor
Storage
Other spaces
Kitchen, Balcony
The Black Swan Lee - Lenox, Ascend Hotel Collection
8.3

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Fitness Center · Assigned Parking · On Site Laundry ·
From
$79/night
Check availability
Property
Hotel · 1 Bed
Amenities
Fitness Center
Assigned Parking
On Site Laundry
Air Conditioning
Free Parking
Wheelchair Accessible
Wifi
Furnished
Other spaces
Workspace
Winter in the Berkshires- warm and loved 3 bedroom home

No rating

·
House
·
3 br
·
Sleeps 6
·
Furnished · In Unit Laundry · Air Conditioning ·
From
$80/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Furnished
In Unit Laundry
Air Conditioning
Wifi
Fireplace

Pet-Friendly Vacation Rentals in The Berkshires, MA

Pets are part of the family, so instead of leaving them at home, book one of these pet-friendly vacation rentals in The Berkshires. Read the details of each rental more closely for specific pet policies.
Price drop
Life House, Berkshires
8

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Air Conditioning · Furnished · On Site Laundry ·
From
$289/night
Check availability
Property
Hotel · 1 Bed
Amenities
Air Conditioning
Furnished
On Site Laundry
Residents Lounge
Wheelchair Accessible
Wifi
Assigned Parking
Other spaces
Workspace
Price drop
Country Charmer

No rating

·
Apartment
·
4 br
·
Sleeps 9
·
Private Pool · Air Conditioning · Dishwasher ·
From
$316/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Private Pool
Air Conditioning
Dishwasher
On Site Laundry
Swimming Pool
Oven
Pool
Wifi
Other spaces
Kitchen
Price drop
Hawks Eye Cabin
8

Very good

·
Apartment
·
3 br
·
Sleeps 6
·
Oven · Furnished · Dishwasher ·
From
$187/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Oven
Furnished
Dishwasher
Wifi
On Site Laundry
Other spaces
Kitchen
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Home > Destinations Vacation Rentals > The Berkshires Vacation Rentals
Updated: September 24, 2023