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Lee Rentals

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66 Houses

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$788

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

$359

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 42 minutes

Price per night from

$827

The Gatehouse on Golden Hill

Lee house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$744

** Private Berkshire Escape** Monthly Pricing Available

Lee house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$659

The Heart of Berkshires

Lee house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$386

Great rentals within 20 miles that match your search

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$497

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

$287

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$414

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$166

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$198

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,103

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

$221

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$695

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$210

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$827

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$166

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$166

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$253

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$315

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$248

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$147

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$166

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 10 minutes

Price per night from

$552

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$276

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 0 minutes

Price per night from

$158

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$992

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Stockbridge house

3 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$877

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$271

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$197

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

Price per night from

$478

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!

Price per night from

$168

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$562

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$258

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$255

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

Chesterfield tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 45 minutes

Price per night from

$130

Tentrr Signature Site - The Lodge's Campsite

Richmond tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 45 minutes

Price per night from

$107

Tentrr Signature Site - Berkshire Mountain Hideaway

Richmond tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 45 minutes

Price per night from

$133

Viewing 38 of 66
rentals in Lee

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Top Destination reviews

Perfect Getaway for Body, Mind and Soul
Fantastic home in an absolutely perfect location

I didn't want to leave. It was the most relaxing and tranquil time I could have imagined. The house is lovely and extremely comfortable -- clean, cozy and situated close to a stunning lake. Spent most of the time cuddled up on the window seat reading and napping. The outdoor hammock was also a treat. The home was also close by to shopping, hiking and cultural attractions so it felt like we had the perfect balance of quiet time and fun and adventure! Will certainly be returning again soon!see more

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