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!
Great Barrington, MA Vacation Rentals. Vacation rentals in Great Barrington, MA make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals in the Great Barrington area. Whether it’s a vacation home, apartment, or condo, each vacation rental offers a truly unique lodging experience. In addition to Great Barrington, 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.
Great Barrington, MA
Southern Berkshire Vacation Rentals
Modern Victorian Walk To Town/Close To 2 Ski Resorts! Great Neighborhood, Gardens, Covered Porch, Screened Deck & Fenced Yard.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Apartment In Gorgeous Stonybrook Farm, Renovated Barn, Hiking, Biking, Canoeing, Golfing, Nature Tours, & Historic House Tours.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Romantic Berkshires Cottage – Stunning Views, Shared Pool, Unsurpassed Scenery, Minutes From Downtown Great Barrington.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Ranch On 5+ Acres & 0.7 Mi To GB Main St. Sleeps 10 + Wi-Fi + HOT TUB, Large Front Porch, Lawn Games, Fire Pit, Outdoor Grill.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Great Barrington Walkable To Lake & Town! Huge TV, Board Games And A Foosball Table, Well Stocked Galley Style Kitchen.
Sleeps: 11
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Family Home w/Big Yard On The Hill, Short Walk To Downtown And Lake Mansfield, Piano, Mountain Views, Lawn Furniture.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Great Barrington Getaway: Lake Access, Water Views, Swimming, Hiking & Endless Lakeside Fun Awaits, Wraparound Deck, Perfect Retreat.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Great Barrington, Cabin Sleeps 14, PRIME Location In Downtown Great Barrington, Sit On The Huge Deck In Teak Rocking Chairs.
Sleeps: 14
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
NEWLY REMODELED COUNTRY CASTLE, Spectacular Hiking, Biking, Extraordinarily Comfortable, Beautiful Property.
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Home In Great Barrington, Enjoy Sunset Views, Steps Away From Historic Downtown Great Barrington & East Mountain Hiking Trails.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Modern Cottage Minutes From Downtown Great Barrington, Quick Access To Tanglewood, Farmers Markets, Shopping, Theatre And More!
Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Idyllic Berkshire Get Away: Balance Of Relaxation & Convenience, Screened Porch, Wet Bar, Pool Table, 50” Plasma TV.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
A Fun Farmhouse Near Ski Butternut, Unique Shops & Restaurants, Video Games, Ping Pong & Air Hockey Tables, Corn Hole Game.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Charming 1905 Mill House, Secluded, Yet Walking Distance To Main Street Stores, Corner Property, Adjacent To The River.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Classic Antique Berkshire Farmhouse w/Heated Pool & Modern Amenities, Treehouse & Apple And Pear Orchard, Beautiful Landscaping.
Sleeps: 11
Bedrooms: 3
Bathrooms: 3.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Lakefront Berkshires Retreat w/Deck, Dock & Boat! Woodsy-Style Decor, Sportsman’s Paradise, Hike, Fish, Swim, Boat.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Renovated Private Guest House By Evergreen Home, Hiking Just Steps Away w/Beautiful Views, Amazing Location, Cute Spot! CLEAN.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Mason’s Lodge · Luxury Home – 3 Fireplaces Mins To Ski & Town, Warm & Welcoming Home, Immaculate & Well Decorated, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Luxe Log Cabin Minutes From Skiing, Hiking, & More, Fun Room For The Kids, Remote & Peaceful, Walk To Everything, Great Location.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Half Moon By AvantStay | 4BR Cabin w/Large Deck & Yard, Covered Outdoor Dining Area, Woodsy Retreat Packed With Style.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Stay In Town, Enjoy Late Check Out, Quiet Residential Street, Spacious Deck, Adults Only Please, 5 Min. Stroll To Main Street.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Classic Berkshires Cottage In Sun-Drenched Meadow, Enjoy Mountain Biking At Catamount, Hiking Waterfalls At Bash Bish Falls.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Spacious Berkshires Retreat ~ 3 Mi To Skiing! Piano, Pool Table, Board Games, Screened-In Porch, Yard, Deck, Grill.
Sleeps: 12
Bedrooms: 5
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Cozy Great Barrington Home ~ 1 Mi To Ski Resort! Ideal Spot For Your Weekend Getaway w/Friends! Stop By The Naumkeag.
Sleeps: 9
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Lakeside Retreat Just You, The Lake & The View! Scenic Views, Outdoor Spaces – Deck, Screened Porch, Private Lake Access.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Location Location! Comfort & Privacy, So Close To Downtown, Play Croquet Or Badminton On The Lawn, Swim At Lake Mansfield.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Beautiful House In The Woods, Huge Yard, Hot Tub, Several Swimmable Lakes And Rivers, Hiking Trails, Nature Preserves, Playgrounds.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Berkshire Cottage – Seasonal Rentals Highly Encouraged! Min From Downtown Great Barrington & Stockbridge, Tanglewood.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Gem Of The Berkshires, Mountain View, Short Walk To Lake & Downtown, Close To Tanglewood & Jacob’s Pillow & More.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Private Berkshires Getaway Minutes To Ski Butternut, 2 Min Drive To Ski Butternut, 8 Min To Downtown Great Barrington.
Sleeps: 6
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Mac Mountain House: Berkshire Ski Retreat, Fire Pit, You’ll Find Everything From Gourmet Food & Coffee Shops, Yoga & More!
Sleeps: 10
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Modern Riverside Cottage In Hip Walkable Community, Large Modern Kitchen, Formal Dining Room, Comfortable Living Room.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
2BR Riverhouse In The Heart Of The Berkshires, Located On The Bank Of Rising Pond Of The Housatonic River, Unique Appeal.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Twin Maple Farm: Charming Modern Farmhouse, 20 Minute Radius There Are Ski Areas, Hiking Trails, Waterfalls, Museums.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Sunsets On Blue Hill, Newly Renovated Farmhouse, Quiet Neighborhood, Wrap Around Porch w/Sunset Views, Chef’s Kitchen.
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Family Vacation Home In Great Barrington, 1 Week Minimum, Lovely Boutiques, Screened Porch, Spacious Front & Back Yards.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Minutes From Ski Butternut, Tanglewood, & Downtown Great Barrington, Former Tavern & Stage Coach Inn, Perfect Getaway.
Sleeps: 15
Bedrooms: 7
Bathrooms: 6.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Light-Filled 3BR Home w/Fireplace & 3.5 Miles From Butternut Ski Area, Relax On The Mahogany Porch , Ping Pong Table.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Renovated Family Friendly House Close To Everything & Endless Views, Ping Pong Table, Swing Set & Slide, Outdoor Fire Pit.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Berkshires Estate w/Heated Pool by Evergreen Home, Pool House w/Kitchenette, Stunning Views, Ideal For Large Groups.
Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Eastbungalow, Lg Duplex Apt, Porch, Walking Distance To Town, Close To Tanglewood, Norman Rockwell Museum & Bash Bish Falls.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Magical Country Retreat In The Berkshires, Ping Pong Table, A Vacation Paradise For All Seasons, Hot Tub On The Porch.
Sleeps: 16
Bedrooms: 9
Bathrooms: 9.5
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Rosecliff: Ultra-Lux Pool, Big Views, Green River, Sleeps 15, Pool House, Mountain Views, Sun Room, Gas & Wood Burning Fireplaces.
Sleeps: 15
Bedrooms: 6
Bathrooms: 6.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
Gorgeous Contemporary Estate! Monthly Rental. WALK TO TOWN!!! Woods For Hiking, Fire Pit, Ping Pong Table, Private Hot Tub.
Sleeps: 8
Bedrooms: 5
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
A Perfect Getaway Year-Round, Booking For The Rest Of 2024! Pool, Fire Pit All Ready For You, Shoot Pool, Play Games, Stream Movies.
Sleeps: 12
Bedrooms: 5
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Spacious, In-Town, Steinway Grand, Lg & Comfortable, Hammock & Wicker Furniture On Porch, Beautiful Old Apple Tree, Gardens.
Sleeps: 6
Bedrooms: 4
Bathrooms: 4.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Vacation Rentals
A Four-Season Forest Cabin, Perfect Time To Get Away, Swim In A Nearby Lake, Foliage Is One Of The Best! Very Private.
Sleeps: 8
Bedrooms: 5
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Vacation Rentals
Berkshires Chic & Cozy, Historic Home Sleeps 10, Amazing Nature Views, Feel Like You’re In The Serene Country, Great Location!!!
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome