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Monterey Rentals

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61 Results

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61 Houses

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 10 minutes

Price per night from

$565

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$202

Great rentals within 20 miles that match your search

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$198

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

$367

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

$294

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$311

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

$847

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$170

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 25 minutes

Price per night from

$226

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$203

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

$226

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$806

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$847

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,129

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$170

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$170

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$322

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$282

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 0 minutes

Price per night from

$162

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Stockbridge house

3 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$897

Tentrr Signature Site - Great Barrington Campsite - With Pool!

Great Barrington tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 45 minutes

Price per night from

$102

The Heart of Berkshires

Lee house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$395

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$277

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

$169

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$282

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$565

The Cottage at Great Falls

Falls Village cottage

2 bedrooms / 1 bathroom / sleeps 4

“Relaxation Overload” Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep. Amazing art? Yep! This place is incredibly decorated and if you forgot anything there is a 99% chance there is an extra in the house. When we arrived everything was set up perfectly and the fire place even had a "Light Here" sign. I highly recommend this place and Danielle was amazing to work with. Every question was answered and she was very polite. This is a need to visit place!

Responds fast! avg. 3 hours 54 minutes

Price per night from

$271

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$516

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

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

$487

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$263

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$218

Tentrr Signature Site - Berkshire Mountain Hideaway

Richmond tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 44 minutes

Price per night from

$136

Tentrr State Park Site - NY Taconic State Park: High Valley Rd Site E

Copake Falls tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 44 minutes

Price per night from

$155

Tentrr State Park Site - NY Taconic State Park: Orphan Rd Site C

Copake Falls tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 44 minutes

Price per night from

$155

Tentrr Signature Site - Running Spring Farm

Tyringham tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 44 minutes

Price per night from

$115

Tentrr State Park Site - NY Taconic State Park: Orphan Rd Site B

Copake Falls tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 44 minutes

Price per night from

$155

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