Vacation rentals in the Southern Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals in Great Barrington. 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 Great Barrington area. Many vacation rentals are located within a short distance to one of our wonderful local attractions including, theatre, skiing, golfing, fishing, hiking, boating, and an array of restaurants for you to choose from.
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
2 Bedroom, 1 Bathroom, Riverhouse In The Heart Of The Berkshires, Spectacular Views, Tanglewood, Shakespeare And Co.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Home in Great Barrington, Steps To East Mountain Hiking Trails, Enjoy Sunset Views, Enjoy The Comfort, Charm, And Privacy.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Renovated Private Guest House, Hiking Steps Away w/Beautiful Views Of Mountains & Long Pond, 14 Minutes To Butternut.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Romantic Berkshires Cottage – Stunning Views, Pool, All Seasons are alive w/Beauty, Rolling Hills & Verdant Meadows.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR Cabin w/Large Deck & Yard, Covered Outdoor Dining Area, Visit Berkshire Botanical Gardens, Bidwell House Museum.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
New Home In The Berkshires. Fire Pit, Barrell Hot Tub, Gas Grill, Private & Quiet. Great Location, Close To Stockbridge.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Lakeside Retreat Just You, The Lake & The View! Deck, Screened Porch, Private Lake Access, Tranquility & Adventure.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Zen Riverfront Studio w/Spa Steam Shower, Wood Stove, SKI Catamount/Butternut, Perfect For Couples Or Solo Travelers.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4 Bedroom, 4 Bath Great Barrington Lakeside Getaway With Kayak & Grill, Stunning Water Views And Lakeside Fun, 2 Large Decks.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stunning Renovated Victorian, Blueberry Bushes, Maple Tree, Lawns, Mature Flowers, & Custom Cobblestone, 15 Min Walk From Downtown.
Sleeps: 12
Bedrooms: 5
Bathrooms: 4.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Idyllic Retreat; Hot Tub/Sauna, 15 Min From Butternut, Full Gym, Amazing Location Central To All The Berkshires Has To Offer!
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Butternut SKI 4 miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St, Wi-Fi + HOT TUB, WINTER Skiing And Snowboarding.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Gem Of The Berkshires, Mountain View, Short Walk To Lake & Downtown, Breathtaking Views, Screened Porch, Incredibly Clean.
Sleeps: 12
Bedrooms: 5
Bathrooms: 4.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful House In The Woods, Huge Yard, Hot Tub, Fire Pit, Peloton Bike & Peloton Treadmill, Gas Grill, Lounge Chairs.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tranquil 2BR House w/Woodland & Pasture Views In Great Barrington, Finest Walking & Cycling Routes, Kickback, Relax & Enjoy.
Sleeps: 5
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Large 3 Bedroom House w/WiFi & Air Conditioning In Great Barrington, Relax In Comfort, Inground Pool, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Long Pond Vacation Home In The Berkshires, Screened Porch & Patio, Spa, Upside Down Converted Barn.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington Get Away, Steps Away From Downtown GB, Huge Backyard Right On The Housatonic River, Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
An In-Town Beauty with Late Checkout, 5 Min Stroll To Main St., Close To Tanglewood, Appalachian Trail, Rockwell Museum.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Mason’s Lodge · Luxury Home – 3 Fireplaces, Mins To Ski Butternut & Town, Pizza Oven, Brick Patio w/Outdoor Seating.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Vacation Home In Great Barrington, 1 Week Minimum, Tanglewood 20 Min Away, Lovely Boutiques, Screened Porch.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
5BR, 3BA, Sleeps 12 – The Pool Is Open, 2 Fireplaces, 2 Miles From Great Barrington, 5 Min From Ski Butternut.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Simply Elegant Log Home, Only 3 Minutes From Butternut! Recently Renovated! 3 Fireplaces, Quick Drive To Great Barrington.
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Great Escape Ski Cottage w/HOT TUB Overlooking The Open Forest View, Festivals & Hiking Trails, Air Hockey Table, Foosball Table.
Sleeps: 16
Bedrooms: 5
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Sunsets On Blue Hill, Newly Renovated Farmhouse, Wrap Around Porch, Hike, Bike Ride, Large Fenced Yard For Children & Pets.
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshires/Great Barrington Chic & Cozy, 4 Bedrooms, Sleeps 10, GB Is Hip & Charming, Great Restaurants & Attractions, Skiing.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Impeccable House Minutes From Downtown Great Barrington, Easy Access To The World’s Cultural Epicenter, Finished Basement!
Sleeps: 8
Bedrooms: 4
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Contemporary 3BR Home w/Views, Fireplace & Close To Butternut Ski Area, Bsmt. Game Rm, Propane Fire Table On Front Porch.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets