Lee Rentals

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53 Houses

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

Price per night from

$814

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

Price per night from

$371

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$855

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$740

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$655

Great rentals within 20 miles that match your search

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$257

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$152

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$325

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$171

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$171

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$261

Berkshire Farmhouse Vacation

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Price per night from

$297

Escape to the Berkshires!

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 11 minutes

Price per night from

$314

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$428

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$171

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$285

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

Price per night from

$170

Gartner House, a charming home in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

Price per night from

$228

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$718

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$217

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$855

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

Price per night from

$204

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$1,140

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$570

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$342

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$456

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$569

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$569

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$195

Chalet near 4 ski resorts with hot tub

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,025

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$683

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$259

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$280

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$114

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$564

Garfield House

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$200

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Price per night from

$1,259

Viewing 38 of 53
rentals in Lee

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