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!
Lenox, MA Vacation Rentals. Vacation rentals in Lenox, MA make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals in the downtown Lenox area, and a short distance from Tanglewood. Whether it’s a vacation home, apartment, or condo, each vacation rental offers a truly unique lodging experience. In addition to Lenox, 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.
Lenox, MA
Central Berkshire Vacation Rentals
Unique Condo, Quiet Neighborhood, Walk To Town, Access To A Small Yard, Great For Kids 8 & Older Please, Great Location!!
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Vacation Or Work Away From Home! Private Beach Lakefront 3 Season Cottage In Lenox MA, Screened Porch, Panoramic Views.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
51 Church Street, Lenox MA – 1BR Unit, Fully Equipped, Refined Getaway, Unit Has Natural Light, Relaxed Environment.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
5 STAR CASUAL ELEGANCE For 5 STAR GUESTS, HYDRANGEA HILL, comfortable wicker outdoor seating, Grill, Fire Pit, Great Location!!!!
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Your Invited To The Berkshires! Location, Privacy & Charm! Close To Downtown Lenox, Unique Shopping, Cafes, The Outdoors.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! Renovated 1770s Stage Coach Stop, Rental Apartment Space.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Historical Downtown 1BR, Peaceful, Well Designed, Full Of Amenities, Location Could Not Be Better, Steps Away From Everything.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Beautiful Lenox Home, 3 Mi To Shakespeare & Co! Spacious Yard, Cozy Sunroom, Perfect Location, Close To Many Attractions.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Heart Of Lenox Walk To Town Cozy Cottage! Short Stroll Away For Great Hiking & Biking, Just As Quaint Inside As The Outside!
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
48 Main Street, Lenox MA, Fabulous House And Location! Very Clean And Comfortable, Great Location, Walk To Everything.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Lenox – Walk To Town – Berkshire Home, Beautiful Backyard For Grilling, Explore The Best Of Lenox & The Berkshires Activities.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Enjoy A Renovated Private Home Right In Downtown Lenox, Our Lovely Home Is Literally A Stones Throw From Downtown Shops.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Lenox Grand Colonial w/Pool By Evergreen Home, Quiet Cul-De-Sac Beneath October Mountain, So Close To Everything.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Main Street Delight 1BR, Beautiful Space Fully Equipped For All Your Needs, Walk To Everything, Super Clean, Modern & Convenient.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Colonial House, w/Yard, 7min Walk To Downtown Lenox, A Peaceful Retreat w/A Timeless Aura, Picture Yourself On The Patio.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Private Apartment In The Heart Of Downtown Lenox, Walk To Concerts At Lilac Park, Shops & 5-Star Restaurants, Hiking/Biking.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
New! Inspired Country Retreat In Lenox, Sleeps 8, Memorable Striking Architecture, Close To Skiing & Tanglewood, Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
One Bedroom Luxury Cottage At Blantyre, Relais & Châteaux, Charming Pot-Belly Stove, Overlooks The Perimeter Gardens.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Lenox, Private Setting, Close To Tanglewood, Rents By Month, Full Of Beautiful Music And Theater, Peaceful, Enjoyable.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Huge Designer House On 2 Acres Property, Min. To Restaurants, Museums, Best Hiking Right From Your Doorsteps, Beautifully Furnished.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, Beautiful, Comfortable, Fully Furnished.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
The Kemble- Built By A US Secretary Of State In Lenox, World-Class Amenities, Massive Rolling Views Of The Stockbridge Bowl.
Sleeps: 35
Bedrooms: 13
Bathrooms: 13.5
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
The Winthrop Estate – 12K, SF, 32 Acres, Fire Pit & Expansive Stone Patio, Virtual Reality Gaming Room, Foosball, Bocce, Lawn Croquet.
Sleeps: 24
Bedrooms: 11
Bathrooms: 10.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Luxury Berkshires Retreat In Lenox – Main House & Studio, Close Proximity To Tanglewood, Ski Slopes, Hiking Trails, Lakes.
Sleeps: 15
Bedrooms: 7
Bathrooms: 4.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Newly Renovated 3BR House In Lenox w/Modern Interior Design, Quiet Dead End Street, Short Distance Into Downtown.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Private Guest House In Dtwn Lenox, Walk To Dining! World-Class Arts & Culture, Outdoor Recreation, Museums, Shops, And More.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Heart of Lenox!! – Renovated Downtown Apartment, Fully Equipped For All Your Needs, Clean And Beautifully Decorated.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Walk To Town Apt., Lenox Condo, Outside Picnic Area & Grille – Across From Ventford Hall, Hot Tub, Walk To Everything.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Historic Lenox Village Summer Rental, Walking Distance To Shopping, Dining, Grocery Store, Post Office & Entertainment.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Charming 3BR Townhome Owned By Artist In Wonderful Lenox w/WiFi, AC, Perfect For Your Escape To Lenox, Charming Property.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
The Penthouse, Downtown Lenox Apt. By Evergreen Home, Located Above Bistro Zinc, Not Suitable For Small Children, Quaint Village.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
This Beautiful Dutch Gambrel Is The Ideal Spot For Your Next New England Getaway, Well Equipped Kitchen, Relax In The Hammock.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Sun Filled Lenox Retreat – Min. To Tanglewood, Go For A Hike At Nearby October Mtn., Pleasant Valley Or Tyringham Cobble.
Sleeps: 10
Bedrooms: 3
Bathrooms: 1.5
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Berkshire Vacation Rentals: Private Access To Laurel Lake, Enjoy Lake Life, Experience The Serenity Of Lake Living.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
Village View- Elegant, Comfortable, Historic Home In Downtown Lenox, 140 Year Old House, Home Of Shakespeare & Co. & Tanglewood.
Sleeps: 8
Bedrooms: 5
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Enjoy Comfortable Elegance In This Secluded Grand Home Located In Town, Tastefully Decorated, Walk To Rest., Shops, Art Galleries.
Sleeps: 9
Bedrooms: 5
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Historic Lenox 5BR/5BA Renovated Luxury House On 6 Acres, Minutes To Tanglewood, Gourmet Chef Kitchen, Porch & Sun Room.
Sleeps: 10
Bedrooms: 6
Bathrooms: 5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Renovated 1860’s Farmhouse, Across From The Miraval, Walk Or Bike To Town, Perfect For An Extended Family, Fire Pit, Hammock.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Lenox, MA
Central Berkshire Vacation Rentals
The Best Of Both Worlds, Country & Culture, Large Kitchen w/A Prep Pantry, View Of October Mountain, 5 Min To Downtown Lenox.
Sleeps: 8
Bedrooms: 5
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Steps Away From Shops & Restaurants Of Lenox Village, w/Private Forest, Steps Away From Lilac Park, Boutiques, Loop Walking Trail.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Beautiful, Secluded, Private Resort In The Heart Of The Berkshires In Lenox, MA, Scenic Area, Indoor & Outdoor Pools, Hot Tub.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Vacation Rentals
Cozy Condo, Walk To Town, Private & Bright, Located On The Second Floor, Walk To Kennedy Park For Great Hiking, Large Outdoor Area.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1.5
No Pets