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!
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Park Street Penthouse Apartment, Walk To Adams Theater, Firehouse Cafe, AJ’s Trail Pub, Hike Or Visit MASS MoCA, The Clark Art.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1.5
No Pets
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Cozy Home In The Berkshires, Fenced In Yard! Swim At Windsor Lake, Catch A Concert At Tanglewood Or MassMoca.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Berkshires Family Fun! Kid-Friendly Getaway Near Skiing, Hiking, Museums, Breathtaking Countryside & Mountain Views.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Golf House By Mt Greylock – Walkable Adventures! Large Yard & Cozy Spots To Unwind, Easy Walk To Downtown Adams.
Sleeps: 7
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Winter Berkshires Retreat! Dog Friendly, Hot Tub, Shopping, Snow Sports, Private Canoe, Appalachian Trail Hiking.
Sleeps: 7
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot Jacob’s Pillow, Tanglewood, Norman Rockwell Museum.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Peace And Quiet On The Lake, Close To Tanglewood, Jacobs Pillow, Lee Outlets, Theater, Go Kayaking, concerts, skiing.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Quiet Comfortable 2 Bedroom, 1 Bath Cabin 5 Minute Walk To Swimming And Boating, Screened-In Porch, Just Relax And Have Fun.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Unique Tranquil Octagonal Retreat W/Red Cedar Barrel Sauna, Min. To Jacobs Pillow Dance & Ski Resorts.
Sleeps: 7
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Becket Home w/3-Season Porch: Walk To Lake Access, Unwind And Embrace Nature, Views Of Lake, Stroll To Sherwood Shoppe.
Sleeps: 7
Bedrooms: 2
Bathrooms: 1
No Pets
Cheshire, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Lakefront Retreat, Breathtaking Year Round Views, Chef’s Dream Kitchen, Golf Cart, Ping Pong & Air Hockey Tables.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Cheshire, MA
Central Berkshire Area
Berkshire Vacation Rentals
19th c. Barn In The Berkshires, Mtn. Views, A Rushing Swimmable Brook, 2 Adjoining Decks, Beautiful Trout Stocked Brook.
Sleeps: 9
Bedrooms: 3
Bathrooms: 2
No Pets
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Bright, Relaxing 2-Story Built In 1843, w/WiFi & Smart TVs, Open Front Porch & Enclosed Back Porch (Shared), Waconah Falls.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Entire Home In Dalton, Perfect Place For A Getaway, Jacob’s Pillow, Hiking Trails, Skiing, Mass MoCA, & The Clark Art Institute.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Brooksong, The Perfect Berkshires Getaway, Play Pool, Sip Cocktails At The Antique 1920s Bar, Fire Pit, Wahconah Falls State Park.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Hideaway: Berkshire Home – Village Of Egremont, Close To Hiking, Biking, Shopping, Skiing And The Arts!
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful Period Home In The Berkshires, Two Screened-In Porches, Sits Adjacent To The Appalachian Trail.
Sleeps: 4
Bedrooms: 3
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Cottage w/Sauna, Close To Hiking Trails, Ski Lodges & Great Barrington, Wrap Around Deck.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Catamount, Zip Line, Private Setting, Book Now! Porch & Deck, Gas Grill, Short Drive To Many Hiking Trails, 12 Min to GB.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Historic 2-Bedroom 1800’s Carriage House, 8-Minutes To Catamount Adventures, Immerse Yourself In The Tranquil Ambiance.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Private Estate, Heated Year Round Outdoor Pool, Former Horse Farm Turned Luxury Vacation Rental, Babbling Brook.
Sleeps: 17
Bedrooms: 7
Bathrooms: 4.5
Pets Welcome
Florida, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Florida Mountain Stylish Custom Built Log Cabin! Located On The Mohawk Trail, Close To Ski Resorts, Beautiful Views.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Florida, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Peaceful Mountain Cabin In The Berkshires, Escape To A World Of Tranquility, Nearby Hiking Trails, Scenic Drives, Waterfalls.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
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
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
Charming 3BR Chic Farmhouse Within Walking Distance Of Great Barrington, Min Away From Butternut & Catamount.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
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
BAGELS & SLOPES: The Ultimate Ski Getaway – Start Your Day Deliciously, Hit Powder Perfectly! Kitchen Is Fully Stocked, Large Back Porch.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
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
Classic Antique Berkshire Farmhouse w/Heated Pool & Modern Amenities, Min From Town, Hiking, & Swimming, Treehouse.
Sleeps: 11
Bedrooms: 3
Bathrooms: 3.5
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