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!
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Off-Season Sabbatical Retreat Rates! Perfect For The Remote Worker, Quiet Retreat For 2, Views Of The Spacious Grounds & Forest.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Walk Into Town, Soak Up Sun On Enclosed Porch & Steps Away From Nature Trails! ‘Secret Gardens’, Fire Pit, Foot Bridge.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Location!!! Location!!! Berkshire Glamour (And Comfort) Meets Town And Country, One Of A Kind Must See Getaway, Comfortable & Decadent.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
A Charming Mid 1800’s Stockbridge Farmhouse, Peaceful Serenity Of The Berkshire Mountains, Tanglewood, The Famous Red Lion Inn.
Sleeps: 6
Bedrooms: 4
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Secluded + Modern, Enclosed Patio, Forest Views, Woodland Zen by AvantStay, This Rental Will Take Your Breath Away, Spacious Deck.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cabin Fever In Stockbridge, The Decor Is Chic & Bohemian Cool! 6 Minutes To Tanglewood, Great Hiking Nearby, Location Is Great.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Delightful Stockbridge House, Walk To Town! Large Backyard & Gardens, Indoor Sauna, Steps Away From Hiking, Shopping, Gardens.
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Home, Come Experience The Berkshires! Screened In Porch, Fire Pit, Great Area To Relax, Well Stocked Kitchen.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tranquil 3BR Stockbridge House w/Private Deck! Fireplace, Venture Off-Site For Skiing At Butternut, Hiking Trails, Location Is Amazing.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Two Blocks From The Red Lion Inn & Next To Berkshire Theater, Great Views, Looks Down Upon The Housatonic River, The Ambiance.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Classic Stockbridge Cottage, Screened-In Porch For Outdoor Dining, Expansive Deck, Has Everything You Need, Convenient Location.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Cape Near Tanglewood & Kripalu – Heart Of The Berkshires! TV Lounge Area In Basement, Huge Deck, Very Clean & Comfortable.
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Home: Walk to Town Beach! Escape To A Lake Retreat, Days Of Fun Boating, Swimming & Kayaking, Various Hiking Trails.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Stockbridge Cabin – Walk To Beach & Lake! Perfectly Located, Tanglewood, The Norman Rockwell Museum & Hiking Trails.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tanglewood, The Norman Rockwell Museum & Hiking Trails, Very Private Setting On The Water, We Have Kayaks, Rowboat, Stand-Up Paddle Board.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Bowl Lake Community, Private Beach, Perfect Place To Relax & Enjoy, Walking, Hiking, Swimming, Kayaking, Skiing.
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Clean & Modern Space w/A Mix Of Original Warmth & Charming Renovation, Great Restaurants, Music Everywhere, A Beautiful Place To Stay.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Artist’s Camp On Lake Mahkeenac, Perfect For A Couples Getaway, 1 Mile From Tanglewood, Great Location, Comfortable, Beautiful Setting.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Loft w/Private Beach On Gorgeous Mountain Lake In The Berkshires, The Area Is Spectacular, Dock For Hanging Out, 5 Kayaks To Use.
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
No Pets
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Enchanted Cottage On Babbling Brook, Screened In Porch, Deck, Town Swimming Pond, Adults Only Please, Spacious And Extremely Cozy.
Sleeps: 6
Bedrooms: 3
Bathrooms: 4
No Pets
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Picture-Perfect Farmhouse Nestled In Berkshire County, MA Near Tanglewood, Beautiful, Classic Farmhouse, Gorgeous Landscape.
Sleeps: 9
Bedrooms: 5
Bathrooms: 3
No Pets
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Luxurious, Family Friendly, Nature Retreat At Meadows Edge! Chefs Kitchen, Designated Playroom For Your Little Ones, Private Pool.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4.5
Pets Welcome
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Treetop Hideaway In Tyringham, Overlooking The Beautiful Tyringham Valley, Screen Porch w/Hot Tub, Peaceful Setting, Great Location.
Sleeps: 8
Bedrooms: 4
Bathrooms: 1
No Pets
Tyringham, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Ashintully Cottage In Spectacular Setting, Landscaped Public Gardens w/Winding Brook, Paths & Hiking Trails, Lovely, Peaceful Place.
Sleeps: 6
Bedrooms: 4
Bathrooms: 3
No Pets
Washington, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Home Rental: Enjoy Berkshire Fall Foliage, Pool, Fenced In Area For Pets, Well-Appointed & Cozy, Great Location.
Sleeps: 8
Bedrooms: 4
Bathrooms: 1
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR Home w/Beautiful Gardens On Pond In Berkshires. Walking Distance To Town, Gazebo, Bar Area, Dock Access, Multi Tiered Deck.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Sophisticated & Secluded Lenox Mt Retreat, Minutes From Tanglewood. New listing, Game Room, Fitness Equipment, Cozy Ambience.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Vacation In A Berkshire Farmhouse, Enjoy The Tranquility & Comfort, Babbling Brook, Gorgeous Screened-In Porch, Cool And Calming.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming 3BR In-Town House w/AC and WiFi In Tranquil West Stockbridge, In Town You’ll Find Antiques, Galleries, Gift Shops, Rare Bookstore.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4.5
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Secluded Mountaintop Retreat In The Heart Of The Berkshires, Basement Den, Eclectic Antique Furnishings, Wonderful Place To Stay.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3.5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
West Stockbridge Sanctuary by Evergreen Home, Enjoy Quiet Country Living, Propane Fire Pit, Close To All Of The Attractions.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern Cabin Near Tanglewood, Restaurants, Hiking Trails, Waterfalls & Lakes Less Than A Mile Away, Come Hang And Enjoy.
Sleeps: 9
Bedrooms: 4
Bathrooms: 2
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Enchanting Country House On 18 Acres, Sunset Views, <15 Minutes From Tanglewood, Large Fenced-In Dog Pen, Peaceful & Lush Surroundings.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Light-Filled Family Home. Book Now For The Summer! Screened Porch, Wrap Around Covered Deck To Enjoy Sunsets In The Backyard.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Indoor Pool & Lofted Game Area, Sunroom w/Sweeping Mountain Views, Wellspring, Perfect For Groups, Lofted Game Area, Great Location.
Sleeps: 12
Bedrooms: 7
Bathrooms: 4.5
No Pet
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Expansive Rustic & Modern Berkshires Estate On 66 Acres, Mountain Views…Pool, Sauna, Outdoor Shower, Fire Pit, Great Location!!!
Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Panoramic Views, Indoor Pool By Evergreen Home, Plenty Of Hiking, Patio And Fire Pit, Beautiful And So Nicely Furnished.
Sleeps: 11
Bedrooms: 4
Bathrooms: 4.5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Crossbridge: Vintage Charm + Unique Character, Covered Porch, Spiral Staircase, Peaceful Getaway & Quality Time, Scenic Outdoor Views.
Sleeps: 7
Bedrooms: 4
Bathrooms: 5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Serene Rustic Cabin In The Berkshires! Romance & Seclusion Awaits, Enjoy Quiet Mountain Serenity, Tanglewood (5 Mins), Hiking (2 Mins).
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
New Home – Heart of Williamstown 183, Contemporary Design, Gourmet Kitchen, Hiking & Restaurants Are Close, Great Place To Stay.
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Contemporary Berkshire Home w/Views Of Taconic Golf Course, Discover Peace & Beauty, Perfect Place For Nature Walks. Perfect Location.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk To Spring St! Yard & Deck, Walk To Restaurants And The Clark.
Sleeps: 10
Bedrooms: 5
Bathrooms: 5.5
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Large, Family-Friendly Farmhouse Located In The Beautiful Berkshires, Large Deck, Fire Pit, Plenty Of Land For Hiking, Great Location.
Sleeps: 14
Bedrooms: 7
Bathrooms: 2.5
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Charming Downtown Williamstown Cottage – 5 Min Walk To Campus, Walk To The Theatre, Shopping & Restaurants, Covered Front Porch.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Charming 3BR Condo w/WiFi In Williamstown, MA, Additional Living Room Space With A Cozy Futon, Enjoy A Relaxing stay. Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
New Studio In Town, By The Water, Just Steps Away From Shops, Restaurants, Williams College, Wooded Riverbank, Great For Relaxing.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
NEW! Berkshire Bliss. Cheery & Comfortable Private Home In Williamstown Center, Absolutely Adorable, Large Yard With A Fire Pit.
Sleeps: 5
Bedrooms: 3
Bathrooms: 1
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Williamstown Stay, Minutes To Williams College, Fully Equipped Kitchen, Deck w/Grill, Peaceful Cul-de-sac, Bright And Welcoming.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Secluded Estate: Hot Tub, Walking Path To Downtown, Unparalleled Views, Absolute Killer Location, Relax, Spread Out, And Enjoy Nature.
Sleeps: 16
Bedrooms: 5
Bathrooms: 4.5
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
1 Mi To Downtown: Beautiful Home In Williamstown! Near Hiking Trails, Fire Pit w/Seating, Game Room w/Ping-Pong Table, Books.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
The Brookman: Renovated 6000 SF Estate On 40 Acres, Foosball Table, Ping Pong And Pool Tables, Exercise Equipment, Great Location.
Sleeps: 16
Bedrooms: 7
Bathrooms: 5
No Pets