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!
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Unique Condo, Quiet Neighborhood, Walk To Town, Convenient To The Mountains, Clean & Warm, Rest. & Charming Shops Close By.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Vacation Or Work Away From Home! Private Beach Lakefront Cottage, Perfect Place For Rest & Relaxation, Panoramic Views.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Heart Of Lenox, Walk To Town Cozy Cottage! Right In The Heart Of Lenox, Great Hiking & Biking, Clean & Well Appointed Space.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
5 Star Casual Elegance For 5 Star Guests, Walk To Town, Come, Relax, Enjoy, Immerse Yourself In A Berkshire Winter Wonderland.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Main Street Delight 1BR, Fully Equipped, Few Spa Locations, Location Couldn’t Be Better, Right In The Heart Of Everything.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Enjoy A Renovated Private Home Right In Downtown Lenox, Shops & Fabulous Restaurants, Very Quiet Neighborhood.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Heart Of Lenox!! – Renovated Downtown Apt., Beautiful & Comfortable, Easy Access To Ski Slopes, Unbeatable Location.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Private Access To Laurel Lake, Enjoy Lake Life, Lg Outdoor Deck w/Grill, Go Kayaking Or Swimming, 2 Kayaks & 4 Life Jackets.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy 3 Bedroom Home With Yard & Patio, 5 Minutes To Tanglewood, Beautifully Manicured Garden, Spacious Patio, Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Restored 1881 Well Appointed Farm House, Chef’s Kitchen, Small Deck, Enjoy The Berkshires To The Fullest, Stay Here!
Sleeps: 4
Bedrooms: 2
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Family Friendly Raised Cape in the Center of Lenox Vlg., Large Backyard w/Patio, Walk To All Rest, Boutiques, Grocery & Cafes.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Enjoy A Renovated Private Home Right In Lenox, Fabulous Restaurants, 1.1 Miles To Tanglewood, Back Yard w/ Fireplace.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cliffwood Cottage, Private Courtyard Patio, w/In Minutes To Hiking, Dining, Museums, Theater & Tanglewood.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lg. Immaculate Home, 10 Min. Walk To Lenox Center, Min. To Tanglewood, Quiet & Sunny, Perfect Vacation For 1 To 2 Couples.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lenox – Walk To Town – Berkshire Home, Beautiful Backyard For Grilling, Surrounded By Forest, Walk To Shops, Rests. & Grocery.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stay At Beaver Lodge! Country Views, Enclosed Porch, Great Hiking, Lakes, Skiing, Charming Towns, Lake Garfield 3 Min. Drive.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Monterey Family Chalet, Min. To Lake & 10 Min. To Butternut! Relaxing Retreat All Year Round, Love To Hike? Love To Bike?
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires, Blissfully Tranquil Setting, Covered Porch.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Recently Renovated, Steps To Lake Buel, Close To GB & Stockbridge, Sm. Beach & Private Dock, Enjoy Fishing, Swimming.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Monterey Haven < 1/2 Mi To Lake Garfield w/2 Kayaks, Hike The Appalachian Trail, Nestled Among Luxe Lakefront Properties.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cottage Retreat In Heart Of The Berkshires, Fire Pit, Horseshoes, Bocce, Or Corn Hole, Just Min. To Hiking, Biking, Swimming.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshires Hilltop Retreat w Magic View! 15 Min. To Ski Butternut. Please Enjoy Our Little Slice Of Paradise! Wooded Seclusion.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
No Pets
Mount Washington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spring/Summer Mountain Spa Nature Retreat w/15 Acre Trail System, Hot Tub, Dry Sauna, Hiking Trails, Perfect Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Mount Washington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful Berkshires Colonial On 7 Acres, Everything Is Made To Relax & Disconnect, Create Amazing Memories, Great For Kids.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
New Ashford, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Berkshire Gorge House, 15 Min To Williamstown & Jiminy Peak. A Great, Cozy Rustic Retreat And Get Away.
Sleeps: 6
Bedrooms: 5
Bathrooms: 3
No Pets
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Quiet Rustic Cottage w/Shared Lake Access, 2 Minute Walk To The Water, Canoe And Life Jackets For Your Aquatic Adventures.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Family Cottage In Peaceful New Marlborough, Welcome To Birdwatcher’s Paradise! Your Getaway Awaits!
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Meadow Top Cottage: Countryside Cottage On 72 Acres, Serene Landscape. Fire Pit, Immerse Yourself In The Tranquility.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Cottage Apt., New Marlborough Village Green In The Berkshires, 15 Min From Butternut Ski Basin. 20 Min. To GB.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Pine View Cottage, Berkshires Getaway Lake Buel w/Lake Rights. Appalachian Trail, Butternut Ski Area, Tanglewood.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Converted Berkshire Schoolhouse On A Quiet River, Play Croquet Or Volleyball, Close To Cantina 229, Old Inn On The Green.
Sleeps: 5
Bedrooms: 3
Bathrooms: 1.5
No Pets
New Marlborough, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Peaceful, Post And Beam Loft, Sleeps 9, Everything You Need For A Great Stay. Scrumptious Cafes And Restaurants Nearby.
Sleeps: 9
Bedrooms: 1
Bathrooms: 2
Pets Welcome
New Marlborough, MA
Sothern Berkshire Area
Berkshire Vacation Rentals
NEW LISTING: Cozy Berkshire Cottage 15 Min From GB, Everything You Need For A Great Stay, Mins Away From Hiking Trails
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Cottage On The Lake, Perfect For Kayaking & Fishing, Charming And Restful, Gorgeous View Of The Lake, Fire Pit, Dock.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Cedar Shingle Cottage, Dock, Close To Tanglewood, Jacob’s Pillow Dance Festival, Berkshire Theater Festival & More.
Sleeps: 7
Bedrooms: 3
Bathrooms: 1
No Pets
East Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
East Otis, MA, Waterfront Summer Cottage, Big Pond, Berkshires Most Hidden Treasures, Privately Owned Beach Area.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshires Cabin 2 Mi To Appalachian Trail! Views From The Deck, Beautiful Place, Beautiful Setting In The Woods.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Waterfront Home, Private Get-Away, Incredible Views, Swimming, Kayaking, Canoeing & Pedal Boating.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
East Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR/3BA Lakefront/Ski House In Berkshires. Fully Fitted Kitchen, Hi Speed WiFi, Dock On Otis Reservoir, Beautiful Views.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Meadows House @ Otis Ridge w/7-Person Hot Tub, Shuffleboard Table, Darts & Chess, Backgammon Table.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Peru, MA
Central Berkshire Area
Berkshire Vacation Rentals
Swiss Chalet Style Timber Frame Home In Berkshires w/All Modern Conveniences, Close To Berkshire Lakes, Trails, Arts.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Peru, MA
Central Berkshire Area
Berkshire Vacation Rentals
Remote & Relaxing Cabin, Spend The Day Hiking(Or Snow Shoeing), Firepit, Sled, Very Private w/Wonderful Views.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Peru, MA
Central Berkshire Area
Berkshire Vacation Rentals
The Perfect Escape; Log Cabin Situated On 40 Secluded Acres Of Wilderness, Relaxation And Privacy In Mind, Wrap Around Decks.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming Lakeview Cottage In Heart of the Berkshires, Overlooking Onota Lake, Mtn. Views, Deck, Patio & Gardens.
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
6 Mi To Skiing: Pet-Friendly Home In Pittsfield! Private Yard, Patio, Clean And Great Location, Great Hiking Trails.
Sleeps: 5
Bedrooms: 3
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Dancing Horse Lodge, Located On Horse Farm, Many Hiking Trails, Conveniently Located, Tanglewood, Barrington Stage Co.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy Berkshire Cottage w/Fireplace, Relax At This Unique, Tranquil Getaway, Minutes From All The Berkshires’ Offer.
Sleeps: 5
Bedrooms: 3
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Chic Pittsfield Home With A View! Mountain Views, Gourmet Kitchen, The Setting Is Just Magical! Fire Pit, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming 1BR – 4 Star Resort w/Heated Pool, Gym, Wi-Fi, Lot’s More! Museums, Theaters, Concert Halls, Boating, Kayaking.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Featured In A Home & Garden TV Special, 30 South Mountain Road, Minutes From Tanglewood, Berkshire Theater Festivals.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Stylish Berkshire Apartment Conveniently Located In The Center Of Town, Quiet, Spacious, Fully Stocked Kitchen.
Sleeps: 3
Bedrooms: 2
Bathrooms: 1
Pets Welcome