Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. Below, you will find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more!
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Idyllic Berkshire Get Away: Balance
Of Relaxation And Convenience.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Manor Lane – Private Berkshire Estate
One of a Kind French Manor House.
Sleeps: 12
Bedrooms: 4
Bathrooms: 4
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
A Fun Farmhouse For All.
4 Bedroom, 3 Bath, Heated Pool.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Apartment In Gorgeous Stonybrook Farm, Renovated Barn, Hiking, Biking, Canoeing.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Romantic Berkshires Cottage, Stunning Views Of Rolling Hills & Verdant Meadows, Pool.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Ranch On 5+ Acres & 0.7 Mi To GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stay in Town, Late Check Out, No Children, Short Walk To Main St, Tastefully Decorated
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Escape Barrington, Full Chef’s Kitchen, Close To All The Fantastic Cultural Attractions.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Minutes From Ski Butternut, Tanglewood & Downtown Great Barrington.
Sleeps: 15
Bedrooms: 7
Bathrooms: 6.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington Walkable To Lake & Town! Huge TV, Board Games.
Sleeps: 11
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Vacation Home In Great
Barrington On 3 Secluded Acres.
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Barn Apartment In Gorgeous
Stonybrook Farm In The Berkshires.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
CHIC UPDATED DOWNTOWN
Great Barrington, Sleeps 14.
Sleeps: 14
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Berkshires Retreat, 3 Mi To Skiing! Pool Table, Piano, Porch, Yard, Deck.
Sleeps: 12
Bedrooms: 5
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington Compound With
Scenic Mountain Views.
Sleeps: 12
Bedrooms: 6
Bathrooms: 6
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern Victorian On The Hill,
Easy walk to Main Street and Lake.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
New Secluded 3 Bedroom Country
Castle On 3+ Acres.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Twin Maple Farm:
Charming Modern Farmhouse.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Perfect Getaway On 3 Acres:
5 Bedroom, 3 Baths, Sleeps 12.
Sleeps: 12
Bedrooms: 5
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington Getaway: Lake Access, Water Views, Swimming, Hiking.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Private Estate! Pool, Tennis
Court, 5 Min To Town & Ski Resorts
Sleeps: 12
Bedrooms: 4
Bathrooms: 4
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Castle Hill Getaway,
3,475 Sq. Ft. Custom-Built Home.
Sleeps: 6
Bedrooms: 4
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Simply Elegant Log Home, 3 Minutes
From Butternut! Recently Renovated!
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington, Cabin Sleeps 14, PRIME Location In Downtown
Sleeps: 14
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stunning Modern 5 BR Victorian In
Highly Desirable Part Of Town.
Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
This Renovated Home Is The Perfect
Spot For A Berkshire Getaway!.
Sleeps: 7
Bedrooms: 3
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Location Location! Comfort And
Privacy So Close To Downtown.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Hancock, MA
Northern Berkshire Area
Berkshire Vacation Rentals
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming Historic Cottage On
Scenic Road To Mt. Greylock.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Village Carriage House,
Newly Built On 40 Acres.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy Rustic Studio 6 Minute Drive From Jiminy Peak, The Base Of Mt. Greylock.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
New Huge Beautiful House – 16 Acres
2 Miles From Jiminy!
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Perfect House For Large Families Or
Two Families To Share, Jiminy Peak.
Sleeps: 12
Bedrooms: 4
Bathrooms: 3
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Mountain Getaway In The
Heart Of The Berkshires!
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Hearts Desire Is A Furnished Whole House In A Small, Colorful Garden Center.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Monthly/Yearly, All Season Vacation
Rental, Minutes From Jimney Peak!
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets