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!
Luxury 5 Bedroom House On Private 47 Acre Oasis, Heated Pool & Pond Views, Sleeps 10
Spend your private getaway in this Immaculate contemporary home on 47 acres with 3 acre pond, heated gunite pool and private hiking trails. Sunfilled living room with 20 foot ceilings opens to the dining area and eat-in kitchen. Spacious first floor primary suite. Two stories of large outdoor decks for entertaining with views to the pond, pool and beautifully manicured grounds. Four additional beautifully appointed guest rooms. Fully finished lower level with in law suite and fitness area. Quick & easy “back road” access to Tanglewood. Minutes to Mass Pike and Berkshires best attractions!
Pittsfield, MA Vacation Rentals. Vacation rentals in Pittsfield, MA make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals in the Pittsfield area. Whether it’s a vacation home, apartment, or condo, each vacation rental offers a truly unique lodging experience. In addition to Pittsfield, MA view 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 Vacation Rentals
Apartment Newly Remodeled Super Location, Large Covered Porch, Downtown Pittsfield Is 2 Miles, Close To Lakes & Bouquet.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Chic Pittsfield Home w/A View! Secluded Hill Surrounded By Trees & Picturesque Views Of The Mountains, Fire Pit, Great Rental.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Dancing Horse Lodge, On A Horse Farm, Many Hiking Trails, Right Next To Bosquet Ski Area & Berkshire West Athletic Club.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Central Berkshire Bungalow By Evergreen Home, Walkable Residential Neighborhood, Nearby Parks, Shops & Rest, Great Location.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Country Living Just Minutes From Everything! Now Offering Seasonal Discounts! Home Office, Large Deck, Crab Apple Trees.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Family-Centric Berkshire Getaway by Evergreen Home, Museums, Skiing, Lake Life, Hiking, Theaters & Shopping Just A Short Drive.
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Featured In A Home & Garden TV Special, 30 South Mountain Road, Minutes From Tanglewood, Berkshire Theater Festivals.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Beautiful 8BR, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table, Incredible Views, Enjoy Swimming, Boating, Fishing & More.
Sleeps: 25
Bedrooms: 8
Bathrooms: 3
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Historical Colonial Apt. Near Down Town, Walking Distance To The Colonial Theatre, Berkshire Museum & Local Eateries.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Beautiful Waterfront Home w/Deep Water Dock On Onota Lake, huge 3 Season Sun Room, Covered Deck, Great For Water Sports.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Beautiful Home Away From Home, Great Spaces For Small Pets & Extra Guests, Hot Tub, Large Comfortable Spaces, Great Location.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Cozy Berkshire Cottage w/Fireplace, Tranquil Getaway, Min. From Tanglewood, Bousquet & Jiminy Peak Ski Resorts & Museums.
Sleeps: 5
Bedrooms: 3
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Spacious Historic Home In The Berkshires! Large Rooms w/So Much Sunshine, Furniture Is Lovely, Modern In A Good Way.
Sleeps: 9
Bedrooms: 5
Bathrooms: 2
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Berkshire Mountainside Condo, Ski From This Condo To Bousquet Ski Area, Summer Fun At Tanglewood, Barrington Stage, Jacobs Pillow.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Pittsfield Home w/Deck – 12 Mi To Jiminy Peak! Balcony, Deck, Patio, Gazebo, Great For Outdoor Enthusiasts, Feel Cozy.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Charming Apartment In Berkshire Victorian Home, 3rd Floor Penthouse Unit, Rooftop Deck, Special Spot For Everyone’s Needs!
Sleeps: 8
Bedrooms: 3
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Hidden Oasis In The Mountains By Evergreen Home, Sits Atop A Hill In A Very Nice Neighborhood, Views To October Mountain.
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Stylish Berkshire Apartment conveniently Located In The Center Of Town, Fully Stocked Kitchen, Designed For A Travel Worker.
Sleeps: 3
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Casa Do Lago–Waterfront Home w/Private Dock On Pontoosuc Lake, Comfortable, Very Well Stocked, Incredible Views!
Sleeps: 14
Bedrooms: 5
Bathrooms: 2.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Cape Home In The Beautiful Berkshires, Near Lenox & Bousquet, Perfect Place To Relax With Friends & Family, Great Rental.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Fully Equipped Spacious Family Home In The Berkshires, 3.5 Miles To Downtown Lenox, Tanglewood, Kripalu Etc., Great Location.
Sleeps: 7
Bedrooms: 3
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Centrally Located In The Berkshires – Cozy Bungalow In SE Pittsfield! 5 Min From Bousquet Ski Resort, Min From Hiking & Museums.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Tranquil Lake House Getaway On Onota Lake, Beautiful & Peaceful Place, Tranquil, Clean, Very Stress Free, Great Rental.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
A Private 1940s Elegant Estate, Renovated To Modern-Day Luxury – Tanglewood, 5 Min. To Pittsfield, Great! Close To Mountains.
Sleeps: 9
Bedrooms: 5
Bathrooms: 3.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Near Everything, Relaxing & Peaceful Spot, Biking & Hiking Trails.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Lake Front Home in Heart of the Berkshires, Near Jiminy Peak, Amazing Location, Close To Skiing, Hiking, Restaurants, Tanglewood.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Lakeside Home w/Pool, Completely Renovated, On Beautiful Lake Pontoosuc, Huge Family Room Overlooking The Lake, Great Property.
Sleeps: 16
Bedrooms: 6
Bathrooms: 4.5
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
This House Has 4BR/2BA, Extremely Clean, Games & Books Available, Perfect For Your Family’s Weekend Getaway, Gorgeous.
Sleeps: 12
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Spacious Berkshire Summer Rental, Private Dock On Lake 3BR/2BA, Perfect Getaway, Great View Of The Stars At Night, Quiet & Peaceful.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Pittsfield, MA
Central Berkshire Vacation Rentals
Stylish Cottage Located By Pontoosuc Lake w/Lake Views! Kick Back & Relax, Hot Tub By The Rustic Firepit, Adults Only Please.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Vacation Rentals
Serene Condo Retreat In The Scenic Berkshire Mountains, Pool, Activity Center, Arcade Room, Fitness Center, Comfortable.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets