Berkshire Vacation Rentals, Vacation Homes Rentals Berkshires

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!

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

3BR Home w/Lake & Mountain Views, Near Skiing, And Cultural Attractions! New Deck To Enjoy w/BBQ Grill, Great Location.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Apt. Newly Remodeled Super Location, Large Covered Porch, Close To Lakes And 5 Minutes From Bousquet Ski Area.

Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

House w/View In The Berkshires, Deck, Tanglewood, The Mount, Naumkeag, Mass Moca, Clark, Hancock Village, Etc.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Charming Apartment In Berkshire Victorian Home, 3rd Floor Penthouse, Rooftop Deck, Short & Long-Term Rental, Great Location.

Sleeps: 8
Bedrooms: 3
Bathrooms: 1
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Pittsfield Home w/Deck – 12 Mi To Jiminy Peak! Great For Outdoor Enthusiasts, Balcony, Deck, Patio, Gazebo. Park Square.

Sleeps: 10
Bedrooms: 3
Bathrooms: 2.5
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Centrally Located In The Berkshires – Cozy Bungalow In SE Pittsfield! 5 Minutes From Bousquet Ski Resort, 20 To Jiminy.

Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Country Living Just Min. From Everything! Home Office, Lg. Deck, ENORMOUS Yard, Mountain Views, Beautiful Sunrises.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

The Ponds At Foxhollow, Indoor And Outdoor Pool, Tennis Court, Sauna, Fitness Center, Perfect Location, Beautiful Grounds.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Beautiful 8BR, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table, Swimming, Boating, Fishing, Picnicking And More.

Sleeps: 28
Bedrooms: 8
Bathrooms: 3
Pets Welcome

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Stylish, Centrally Located Berkshires Home-Base, 15 Minutes To Lenox & Tanglewood, Theater Room, Corn Hole Game.

Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Elegant Pittsfield Home Near Downtown & Skiing! Foosball Table, Screened Porch, Catch Live Music At Tanglewood.

Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Welcome

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Lake Front Home In Heart Of The Berkshires, Near Jiminy Peak, Amazing Location, Close To Skiing, Hiking, Restaurants.

Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Beautiful Waterfront Home w/Deep Water Dock On Onota Lake, Sun Room, Covered Deck, Water Sports, Kayaking, Fishing.

Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Renovated Pittsfield Colonial By Evergreen Home, Museums, Tanglewood, Theaters, Hiking, Skiing, Golf, Shopping & Dining.

Sleeps: 12
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Tranquil Lake House Getaway On Onota Lake, 3 Miles To The City, 2 Canoes, 5 Kayaks And A Stand-Up Paddleboard.

Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Solomon Ely Homestead – Charming Pittsfield Stay, Steps From Pittsfield, Wraparound Porch, Filled w/Historic Charm.

Sleeps: 7
Bedrooms: 4
Bathrooms: 1.5
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Hidden Oasis In This Mnt. Home, Hidden Oasis, Hot Tub, Fire Pit, Overlooking October Mountain, Great Location.

Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Fully Equipped Spacious Family Home In The Berkshires, 3.5 Miles To Downtown Lenox, Tanglewood, Kripalu, Ideal Location.

Sleeps: 7
Bedrooms: 3
Bathrooms: 3
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Cape Home In The Beautiful Berkshires – Near Lenox & Bousquet, Wild Acres, Tanglewood, Lenox, Museums, Shopping.

Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Spacious Luxury Berkshire’s Estate On 21 Acres, Pool Table, Air Hockey Table, Foosball Table, Rowing Machine, Sauna Room.

Sleeps: 14
Bedrooms: 6
Bathrooms: 4.5
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Slopeside View: Airy, Luxury Condo w/Pool. Minutes From It All! Miraval, Canyon Ranch, Shakespeare & Co, Tanglewood.

Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
No Pets

Pittsfield, MA

Central Berkshire Area
Berkshire Vacation Rentals

Lakeside Home w/Heated Outdoor Pool-Completely Renovated, On Beautiful Lake Pontoosuc, Perfect For Family Gatherings.

Sleeps: 16
Bedrooms: 6
Bathrooms: 4.5
No Pets