The Berkshires Vacation Rentals
PRICE PER NIGHT
ACCOMMODATION TYPES
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
10
Excellent
·
House
·
4 br
·
Sleeps 9
·
Garden · Toiletries · Tv ·
From
$224/nightProperty
House · 4 Beds · 2 baths
Amenities
Toiletries
Tv
Microwave
Central Heat
Free Parking
Dishwasher
Oven
Wifi
Other spaces
Garden, Kitchen
NEW! Stockbridge Home - Walk to Lakefront Beach!
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Toiletries · Cable · Lake ·
From
$155/nightProperty
House · 3 Beds · 1 bath
Amenities
Toiletries
Cable
Lake
Tv
Microwave
Air Conditioning
Free Parking
Fireplace
Other spaces
Kitchen
1 Bedroom+Loft, Sleeps 9, Bring The Whole Family!
10
Excellent
·
House
·
1 br
·
Sleeps 9
·
Hardwood Floor · Balcony · On Site Laundry ·
From
$302/nightProperty
House · 1 Bed · 2 baths
Amenities
Hardwood Floor
On Site Laundry
Air Conditioning
In Unit Laundry
Dishwasher
Furnished
Wifi
Garage Parking
Other spaces
Balcony, Kitchen
East Otis Romantic Cottage with Deck and BBQ!
9
Excellent
·
Apartment
·
1 br
·
Sleeps 2
·
Outdoor Space · Free Parking · Furnished ·
From
$201/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Furnished
Wifi
Other spaces
Kitchen
Serene Great Barrington Cottage with Fire Pit!
8.7
Very good
·
Apartment
·
1 br
·
Sleeps 4
·
Waterfront · Lake · On Site Laundry ·
From
$242/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Waterfront
Lake
On Site Laundry
Air Conditioning
Free Parking
Furnished
Oven
Wifi
Other spaces
Kitchen
Cozy Great Barrington Home about 1 Mi to Ski Resort!
8.5
Very good
·
Apartment
·
4 br
·
Sleeps 9
·
Free Parking · In Unit Laundry · Dishwasher ·
From
$412/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Free Parking
In Unit Laundry
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Spacious Berkshires Retreat about 3 Mi to Skiing!
No reviews
·
Apartment
·
5 br
·
Sleeps 12
·
Outdoor Space · Air Conditioning · Free Parking ·
From
$994/nightProperty
Apartment · 5 Beds · 3 baths
Amenities
Air Conditioning
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Quality Inn
7.7
Very good
·
Hotel
·
1 br
·
Sleeps 4
·
Ski In Ski Out · Workspace · Air Conditioning ·
From
$99/nightProperty
Hotel · 1 Bed
Amenities
Ski In Ski Out
Air Conditioning
Free Parking
Furnished
Wifi
Other spaces
Workspace
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Historic Huntington Home - Walk to Westfield River
7
Very good
·
Apartment
·
3 br
·
Sleeps 7
·
Free Parking · In Unit Laundry · Fireplace ·
From
$254/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Lenox House with Screened Patio and Mountain View
No reviews
·
Apartment
·
1 br
·
Sleeps 2
·
Pool · Free Parking · In Unit Laundry ·
From
$252/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
Pool
Free Parking
In Unit Laundry
Dishwasher
Furnished
Oven
Wifi
Swimming Pool
Other spaces
Kitchen
The Whitlock
8.1
Very good
·
Hotel
·
1 br
·
Sleeps 4
·
Carpet · Assigned Parking · Ski In Ski Out ·
From
$237/nightProperty
Hotel · 1 Bed
Amenities
Carpet
Assigned Parking
Ski In Ski Out
On Site Laundry
Air Conditioning
Free Parking
Fireplace
Furnished
Life House, Berkshires
8
Very good
·
Hotel
·
1 br
·
Sleeps 4
·
Assigned Parking · Workspace · On Site Laundry ·
From
$273/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
On Site Laundry
Air Conditioning
Free Parking
Furnished
Wifi
Wheelchair Accessible
Residents Lounge
Other spaces
Workspace
Charming Lenox Home View of October Mountain
No reviews
·
Apartment
·
3 br
·
Sleeps 5
·
Pool · Balcony · Air Conditioning ·
From
$437/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Pool
Air Conditioning
Free Parking
In Unit Laundry
Dishwasher
Furnished
Oven
Wifi
Other spaces
Balcony, Kitchen
Picturesque Cottage with Sunroom on Ashmere Lake!
10
Excellent
·
Apartment
·
3 br
·
Sleeps 6
·
Beach · Waterfront · Lake ·
From
$289/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Beach
Waterfront
Lake
Free Parking
In Unit Laundry
Dishwasher
Furnished
Oven
Other spaces
Kitchen
Cozy Monterey Home with Porch Walk to Lake Garfield
No reviews
·
Apartment
·
3 br
·
Sleeps 6
·
Beach · Free Parking · In Unit Laundry ·
From
$275/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Beach
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Charming Historic Home Close to Downtown and Skiing!
No reviews
·
Apartment
·
5 br
·
Sleeps 10
·
Outdoor Space · Free Parking · In Unit Laundry ·
From
$562/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Restored 1800s Home Half Mile to Ski Resort!
No reviews
·
Apartment
·
4 br
·
Sleeps 8
·
On Site Laundry · Air Conditioning · Free Parking ·
From
$353/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
On Site Laundry
Air Conditioning
Free Parking
In Unit Laundry
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Berkshires Cabin 2 Mi to Appalachian Trail!
No reviews
·
Apartment
·
3 br
·
Sleeps 7
·
Free Parking · In Unit Laundry · Fireplace ·
From
$326/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Hilton Garden Inn Lenox Pittsfield
8.5
Very good
·
Hotel
·
1 br
·
Sleeps 4
·
Pool · Workspace · On Site Laundry ·
From
$167/nightProperty
Hotel · 1 Bed
Amenities
Pool
On Site Laundry
Air Conditioning
Free Parking
Fireplace
Furnished
Wifi
Fitness Center
Other spaces
Workspace
Stockbridge Home - Walk to Lakefront Beach!
No reviews
·
Apartment
·
3 br
·
Sleeps 6
·
Beach · Air Conditioning · Free Parking ·
From
$263/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Beach
Air Conditioning
Free Parking
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Updated Canaan Farmhouse Pond and Sunset Views!
10
Excellent
·
Apartment
·
3 br
·
Sleeps 6
·
Outdoor Space · Free Parking · In Unit Laundry ·
From
$309/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Residents Lounge
Other spaces
Kitchen
Pet-Friendly Canaan Home Near Queechy Lake!
No reviews
·
Apartment
·
3 br
·
Sleeps 8
·
Beach · Free Parking · In Unit Laundry ·
From
$261/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Beach
Free Parking
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Berkshires Getaway Close to Gt Barrington, Lakes, Hiking, Skiing
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Hot Tub · Fitness Center · Assigned Parking ·
From
$320/nightProperty
House · 3 Beds · 2 baths
Amenities
Hot Tub
Fitness Center
Assigned Parking
Mountains
On Site Laundry
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Workspace, Kitchen
TreeHouse: Berkshires chalet in sun-dappled forest
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Mountains · Balcony · Outdoor Space ·
From
$382/nightProperty
House · 3 Beds · 3 baths
Amenities
Mountains
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Onsite Management
Other spaces
Balcony, Kitchen
NEW! Austerlitz Home w/ Updated Interior + Porch!
9.7
Excellent
·
House
·
3 br
·
Sleeps 8
·
Toiletries · Tv · Microwave ·
From
$169/nightProperty
House · 3 Beds · 2 baths
Amenities
Toiletries
Tv
Microwave
Central Heat
Air Conditioning
Free Parking
Fireplace
Oven
Other spaces
Kitchen
Charming Historic Home Close to Downtown & Skiing!
9.9
Excellent
·
House
·
5 br
·
Sleeps 10
·
Assigned Parking · Walk In Closets · Garden ·
From
$290/nightProperty
House · 5 Beds · 4 baths
Amenities
Assigned Parking
Walk In Closets
Toiletries
Tv
Microwave
Central Heat
Free Parking
Fireplace
Other spaces
Garden, Kitchen
Tranquil 3BR Stockbridge House w/ Private Deck!
9.3
Excellent
·
House
·
3 br
·
Sleeps 6
·
Cable · Tv · Microwave ·
From
$225/nightProperty
House · 3 Beds · 2 baths
Amenities
Cable
Tv
Microwave
Central Heat
Free Parking
Fireplace
Dishwasher
Oven
Other spaces
Kitchen
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.5
Very good
·
House
·
4 br
·
Sleeps 10
·
Waterfront · Cable · Ceiling Fan ·
From
$279/nightProperty
House · 4 Beds · 2 baths
Amenities
Waterfront
Cable
Ceiling Fan
Mountains
Lake
Tv
Microwave
Central Heat
Other spaces
Kitchen
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.5
Excellent
·
House
·
4 br
·
Sleeps 10
·
Garden · Cable · Ceiling Fan ·
From
$171/nightProperty
House · 4 Beds · 3 baths
Amenities
Cable
Ceiling Fan
Mountains
Lake
Tv
Microwave
Central Heat
Free Parking
Other spaces
Garden, Kitchen
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
9.8
Excellent
·
House
·
3 br
·
Sleeps 6
·
Garden · Toiletries · Cable ·
From
$225/nightProperty
House · 3 Beds · 3 baths
Amenities
Toiletries
Cable
Ceiling Fan
Lake
Tv
Microwave
Central Heat
Free Parking
Other spaces
Garden, Kitchen
PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD
9.8
Excellent
·
Apartment
·
1 br
·
Sleeps 5
·
Fitness Center · Beach · Waterfront ·
From
$270/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Beach
Waterfront
Lake
Air Conditioning
In Unit Laundry
Furnished
Oven
Other spaces
Balcony, Kitchen
Serene Great Barrington Cottage with Fire Pit!
9.8
Excellent
·
House
·
1 br
·
Sleeps 4
·
Walk In Closets · Garden · Toiletries ·
From
$135/nightProperty
House · 1 Bed · 1 bath
Amenities
Walk In Closets
Toiletries
Ceiling Fan
Mountains
Lake
Tv
Microwave
On Site Laundry
Other spaces
Garden, Kitchen
NEW! Spacious & Modern Ashley Falls Home on 1 Acre
10
Excellent
·
House
·
5 br
·
Sleeps 8
·
Walk In Closets · Cable · Ceiling Fan ·
From
$196/nightProperty
House · 5 Beds · 3 baths
Amenities
Walk In Closets
Cable
Ceiling Fan
Tv
Microwave
Central Heat
Air Conditioning
Free Parking
Other spaces
Kitchen
Richmond Pond Beauty
9.5
Excellent
·
House
·
3 br
·
Sleeps 7
·
Waterfront · Ski In Ski Out · Mountains ·
From
$426/nightProperty
House · 3 Beds · 2 baths
Amenities
Waterfront
Ski In Ski Out
Mountains
Lake
Central Heat
Air Conditioning
In Unit Laundry
Fireplace
Other spaces
Workspace, Balcony, Kitchen
Serene Berkshire Artist's House
9.7
Excellent
·
House
·
3 br
·
Sleeps 6
·
Ski In Ski Out · Workspace · Balcony ·
From
$269/nightProperty
House · 3 Beds · 3 baths
Amenities
Ski In Ski Out
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Elevator
Other spaces
Workspace, Balcony, Kitchen
On The Hill, Perfect House With Lots Of Charm!
No reviews
·
House
·
3 br
·
Sleeps 11
·
High Ceilings · Hardwood Floor · On Site Laundry ·
From
$516/nightProperty
House · 3 Beds · 2 baths
Amenities
High Ceilings
Hardwood Floor
On Site Laundry
Central Heat
In Unit Laundry
Fireplace
Dishwasher
Furnished
Other spaces
Kitchen
CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14
9.8
Excellent
·
House
·
3 br
·
Sleeps 14
·
Mountains · Balcony · Air Conditioning ·
From
$828/nightProperty
House · 3 Beds · 3 baths
Amenities
Mountains
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Balcony, Kitchen
Downtown Great Barrington; Enjoy Mountain Views
6
Good
·
House
·
3 br
·
Sleeps 8
·
Mountains · Balcony · On Site Laundry ·
From
$434/nightProperty
House · 3 Beds · 2 baths
Amenities
Mountains
On Site Laundry
Central Heat
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Other spaces
Balcony, Kitchen
The Lenox House. In the center of Lenox and the Berkshires
No reviews
·
House
·
4 br
·
Sleeps 7
·
Fitness Center · Balcony · Air Conditioning ·
From
$312/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Air Conditioning
In Unit Laundry
Dishwasher
Furnished
Oven
Wifi
Other spaces
Balcony, Kitchen
Two Rooms with En-Suite in Quiet Woodland
9.9
Excellent
·
Apartment
·
2 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · In Unit Laundry ·
From
$201/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Kitchen
Beautiful Period Home in the Berkshires
9.8
Excellent
·
House
·
3 br
·
Sleeps 4
·
Ceiling Fan · On Site Laundry · Air Conditioning ·
From
$326/nightProperty
House · 3 Beds · 2 baths
Amenities
Ceiling Fan
On Site Laundry
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Other spaces
Kitchen
History in Huntington - Westfield River Walk
4
Good
·
House
·
3 br
·
Sleeps 7
·
Hardwood Floor · Ceiling Fan · Air Conditioning ·
From
$188/nightProperty
House · 3 Beds · 2 baths
Amenities
Hardwood Floor
Ceiling Fan
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Other spaces
Kitchen
Tranquil 3BR Stockbridge House w/ Private Deck!
9.7
Excellent
·
House
·
3 br
·
Sleeps 6
·
Ski In Ski Out · On Site Laundry · Air Conditioning ·
From
$327/nightProperty
House · 3 Beds · 2 baths
Amenities
Ski In Ski Out
On Site Laundry
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Other spaces
Kitchen
Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn
9.9
Excellent
·
Apartment
·
2 br
·
Sleeps 2
·
High Ceilings · Waterfront · Ski In Ski Out ·
From
$221/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
High Ceilings
Waterfront
Ski In Ski Out
Ceiling Fan
Lake
Furnished
Oven
Wifi
Other spaces
Kitchen
'The Mill River Cabin’ w/ Fireplace & River View!
9.7
Excellent
·
Apartment
·
2 br
·
Sleeps 5
·
Ski In Ski Out · Workspace · Air Conditioning ·
From
$268/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Ski In Ski Out
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
NEW! Stockbridge Home - Walk to Lakefront Beach!
No reviews
·
House
·
3 br
·
Sleeps 6
·
Beach · On Site Laundry · Air Conditioning ·
From
$214/nightProperty
House · 3 Beds · 1 bath
Amenities
Beach
On Site Laundry
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Other spaces
Kitchen
Mid Century Modern, Book & Enjoy The Berkshires
No reviews
·
House
·
2 br
·
Sleeps 4
·
In Unit Laundry · Fireplace · Dishwasher ·
From
$273/nightProperty
House · 2 Beds · 2 baths
Amenities
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Storage
Other spaces
Kitchen
Berkshires Home On 5+ Acres, Rustic & Chic
No reviews
·
House
·
5 br
·
Sleeps 10
·
Hardwood Floor · Workspace · Balcony ·
From
$570/nightProperty
House · 5 Beds · 3 baths
Amenities
Hardwood Floor
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Wifi
Other spaces
Workspace, Balcony, Kitchen
Secluded Cabin On Acres Of Woods
No reviews
·
House
·
3 br
·
Sleeps 8
·
Deck · Carpet · Hardwood Floor ·
From
$534/nightProperty
House · 3 Beds · 2 baths
Amenities
Carpet
Hardwood Floor
Air Conditioning
In Unit Laundry
Fireplace
Dishwasher
Furnished
Oven
Other spaces
Deck, Workspace, Balcony, Kitchen
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.5
Excellent
·
House
·
3 br
·
Sleeps 6
·
Walk In Closets · Garden · Toiletries ·
From
$172/nightProperty
House · 3 Beds · 2 baths
Amenities
Walk In Closets
Toiletries
Cable
Ceiling Fan
Mountains
Lake
Tv
Microwave
Other spaces
Garden, Kitchen
Showing 1 - 50 of 569 results
Updated: March 27, 2023
Learn about vacation rentals in
The Berkshires
Discover 569 vacation rentals near The Berkshires, Massachusetts. This lake community is a good place to getaway, relax, and enjoy the outdoors. Explore nature in this lakeside area. Use our interactive map to find The Berkshires properties near the lake. Whether you’re looking for a nightly rental, 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 near The Berkshires is $99 per night and goes up to as much as $994 per night.
436 of the vacation rentals near The Berkshires are houses.
The average bathroom count for a vacation house near The Berkshires is
2. The average price for vacation houses near The Berkshires is $331 per night. There are 200 vacation homes under this price. The most common
amenities for vacation rentals near The Berkshires are: furnished, wifi, and kitchen. 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
72 available
2 bed rentals
97 available
3 bed rentals
177 available
4+ bed rentals
217 available
The Berkshires Vacation Rentals FAQ
How many The Berkshires vacation rentals are available?
As of March 27, 2023, there are 569 The Berkshires vacation rentals available. Use the filters on Vacations by Zumper to find your next The Berkshires vacation spot.
Are there vacation rentals near The Berkshires that have more than 2 bedrooms?
Currently, there are 491 vacation rentals near The Berkshires that have more than 2 bedrooms. Check each listing to view photos, pricing, and amenities, and contact the listing manager to begin your next vacation today.
How many The Berkshires vacation rentals have internet access?
There are currently 548 The Berkshires vacation rentals that have internet access. See a full list of property features, photos, pricing, and check availability today.
How many vacation rentals near The Berkshires have more than 1 bathroom?
Right now, there are 551 vacation rentals near The Berkshires that have more than 1 bathroom. View vacation spots and check availability for different properties today.
Are there any pet friendly The Berkshires vacation rentals?
As of March 27, 2023, there are 223 pet friendly vacation rentals near The Berkshires. Pet friendly rental policies are managed by the owner. We recommend contacting the listing agent for dog, cat, and other pet policies.
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