Vacation Rentals By Owner In Lenox, MA

$614.35
/ Nightly

Private Vacation Home

Lenox Interlude Stylish Retreat Views, Central Air, Walk to Town

Lenox, Massachusetts, United States
Lenox Interlude is nestled on a quiet cul-de-sac, an easy, seven-minute walk from Lenox village. Designed for guests seeking culture, comfort, and calm. Spend your days exploring galleries & gardens, your evenings at Tanglewood or Barrington Stage, then return home to central air, luxury linens, and deep quiet. Whether your plans include a summer concert, a fall foliage hike, or indulgent spa day, do select this serene, well-appointed home as your base for exploring all the Berkshires offers. While we are new to VRBO, our reviews are all 5 star on other platforms.brbrLenox Interlude is thoughtfully designed for up to three couples -- or a family with adult children -- who want to share a home that stylishly blends comfort, privacy, and quiet sophistication. brbrHere, days unfold at an easy pace. Mornings begin with coffee overlooking the garden, afternoons invite gallery strolls or scenic walks, and evenings end in air-conditioned comfort after a memorable meal or performance. Lenox Interlude is the ideal home base for a culture-rich Berkshires escape.brbrThe home’s layout offers both shared gathering spaces and restful separation, so everyone can travel together without ever feeling crowded.brbrMain LevelbrThe main floor provides effortless one-level living with two queen bedrooms (one with attached bath) and another full bathroom in the hall, making it especially comfortable for couples sharing the space. The welcoming living room with smart TV is perfect for unwinding after a concert or theater outing. The dining room opens to the deck and boasts besutiful views of the Berkshire Hills, while the fully equipped kitchen — complete with a sunny breakfast nook — overlooks the peaceful garden.brbrA bonus twin bedroom offers flexibility for an additional guest or separate sleeping space on the main floor.brbrLower Level Private SuitebrbrIdeal for the couple (or teenager) seeking a bit more privacy, the lower level feels like its own quiet retreat. It features a spacious king bedroom (convertible to two twins with advance notice), a private sitting area with a 60-inch smart television, and convenient access to the laundry room. A dedicated workspace can be added for longer stays.brbrAfter an evening at Tanglewood or a leisurely dinner in Lenox village, stroll home and sink into luxury linens and premium mattresses for a truly restorative night’s sleep. Free parking on site and on street.brbrOther Details:brbrEasy (no big hills to climb) 7 min walk to Lenox village shopping and dining as well as the public tennis/pickleball courts located behind the Lenox Community Center, Shakespeare and Co and The Museum of the Gilded Age. Tanglewood is technically walkable but most people prefer to drive (8 minute drive -- we'll show you the back way). Berkshire Theater Festival, Barrington Stage, The Mount, Norman Rockwell Museum, Berkshire Botanical Garden, Hancock Shaker Village, Naumkeag and Chesterwood, as well as wellness centers like Kripalu, Miraval and Canyon Ranch are all no more than a 15 minute drive away. Golf at Wyndhurst is a 5 min drive. Williamstown (theater festival and the Clark Museum) is 30 minutes, North Adams (Mass MOCA ) 40 minutes. Ski areas: Butternut Basin 25 mins, Bousquet 15 mins, Jiminy Peak 40 mins.

4
Bed

2
Bath

7
Sleeps

Exceptional(150)

$245.74
/ Nightly

Condo

Unique Condo, Quiet Neighborhood, Walk to Town.

Lenox, Massachusetts, United States
Two bedroom, two bathroom condominium in a two family house located in one of Lenox’s most convenient and quiet neighborhoods. Leave your car in the driveway and walk to everything Lenox has to offer! On the first floor is a comfortable living room with queen sleeper sofa, bathroom with shower, washer/dryer, small office space, kitchen w/glass top stove, dishwasher and microwave. Access to a small yard from the kitchen. Upstairs is the master bedroom with king-sized bed, second bedroom has a trundle bed. Full bathroom upstairs.

2
Bed

2
Bath

4
Sleeps

Exceptional(1)

$698.13
/ Nightly

Private Vacation Home

Mid-Century Modern Berkshires Getaway on 6.5 Acres!

Lenox, Massachusetts, United States
Explore The Berkshires while staying in a beautiful mid- century modern deck house. Nestled within nature on a premier road in Lenox with 6 acres of woods that go to Lilly Pond in Stockbridge. Less than a mile from Tanglewood, downtown Lenox, Stockbridge Bowl, hiking trails, Kirpulau, the Mount and many other cultural institutions.

3
Bed

2
Bath

6
Sleeps

Exceptional(150)

$245.74
/ Nightly

Condo

Unique Condo, Quiet Neighborhood, Walk to Town.

Lenox, Massachusetts, United States
Two bedroom, two bathroom condominium in a two family house located in one of Lenox’s most convenient and quiet neighborhoods. Leave your car in the driveway and walk to everything Lenox has to offer! On the first floor is a comfortable living room with queen sleeper sofa, bathroom with shower, washer/dryer, small office space, kitchen w/glass top stove, dishwasher and microwave. Access to a small yard from the kitchen. Upstairs is the master bedroom with king-sized bed, second bedroom has a trundle bed. Full bathroom upstairs.

2
Bed

2
Bath

4
Sleeps

Exceptional(1)

$698.13
/ Nightly

Private Vacation Home

Mid-Century Modern Berkshires Getaway on 6.5 Acres!

Lenox, Massachusetts, United States
Explore The Berkshires while staying in a beautiful mid- century modern deck house. Nestled within nature on a premier road in Lenox with 6 acres of woods that go to Lilly Pond in Stockbridge. Less than a mile from Tanglewood, downtown Lenox, Stockbridge Bowl, hiking trails, Kirpulau, the Mount and many other cultural institutions.

3
Bed

2
Bath

6
Sleeps

Exceptional(1)

$390.02
/ Nightly

Private vacation home

Wooded Berkshire Cottage - Minutes from Lenox Village - A Year-Round Retreat!

Lenox, Massachusetts, United States

2
Bed

1
Bath

4
Sleeps

Exceptional(1)

$510.20
/ Nightly

Private vacation home

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

Lenox, Massachusetts, United States

4
Bed

3
Bath

8
Sleeps

Exceptional(1)

$497.07
/ Nightly

Private vacation home

New for 2025! Walk to Lenox Village - 1930s Cottage Charmer!

Lenox, Massachusetts, United States

2
Bed

1
Bath

4
Sleeps

Exceptional(1)

$486.50
/ Nightly

Private vacation home

Lakefront, Kayaks Included, Come Unwind In Lenox!

Lenox, Massachusetts, United States

4
Bed

3
Bath

10
Sleeps

Exceptional(1)

$481.40
/ Nightly

Private vacation home

Lenox Gem with AC!

Lenox, Massachusetts, United States

3
Bed

2
Bath

5
Sleeps

Exceptional(1)

$457.08
/ Nightly

Apartment

Main Street Delight 1bedroom

Lenox, Massachusetts, United States

1
Bed

1
Bath

4
Sleeps

Exceptional(1)

$423.53
/ Nightly

Private vacation home

5 STAR CASUAL ELEGANCE for 5 STAR GUESTS

Lenox, Massachusetts, United States

3
Bed

2
Bath

6
Sleeps

Exceptional(1)

$398.40
/ Nightly

Apartment

Historical Housatonic Street apartment

Lenox, Massachusetts, United States

1
Bed

2
Bath

2
Sleeps

Exceptional(1)

$245.74
/ Nightly

Condo

Unique Condo, Quiet Neighborhood, Walk to Town.

Lenox, Massachusetts, United States

2
Bed

2
Bath

4
Sleeps

Exceptional(1)

$329.52
/ Nightly

Cottage

Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA

Lenox, Massachusetts, United States

2
Bed

1
Bath

5
Sleeps