COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Monterey Rentals

Updating...

age 0-16
110 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

110 Houses

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$504

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$530

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$212

Pet-Friendly Berkshires Home w/Dock & Fire Pit!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 6 minutes

Price per night from

$275

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 6 minutes

Price per night from

$215

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

$532

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$591

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$177

Price per night from

$699

Charming Farmhouse on Magical 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$464

Riverwood - Cozy Carriage House in the Woods

Falls Village apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$265

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$589

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

$354

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$177

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$148

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$248

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$707

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$206

4 Bedroom Furnished House in Lakeville Connecticut

Lakeville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$383

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$325

Turning Point - Family Retreat & Group Getaway

Great Barrington house

7 bedrooms / 8 bathrooms / sleeps 15

Price per night from

$944

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$177

Charming Private Guest Suite in Historic Village in the Berkshires

New Marlborough studio

Studio / 1 bathroom / sleeps 2

Price per night from

$112

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

$236

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$443

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$118

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$337

Price per night from

$1,174

Ranch at Fox Hollow - Laurel Lake , 4BR's, 4.5 Baths

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$702

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$153

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$885

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$253

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$219

RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 9 minutes

Price per night from

$223

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$708

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Richmond house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$590

Outdoor getaway hunting,fishing,skiing..relaxation

Copake house

3 bedrooms / 2 bathrooms / sleeps 9

“Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas grill, eating on the deck, well stocked kitchen and cozy living room. Spacious, comfortable with a lovely master bedroom with private bath. All bedrooms are located somewhat away from the living room which is nice. Walked to the lake with paddles and canoed with my son; got great coffee at the nearby General Store. Michael is wonderful to rent from and very accommodating.

Price per night from

$224

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$843

Viewing 38 of 110
rentals in Monterey

×

Top Destination reviews

Berkshires House, 40 wooded acres, Lake Frontage
spectacular

This house is pure magic, and so is Karl. Everything was perfect. Cozy nooks everywhere. Beautiful property and woods. everything and more. Cozy beds, clean clean everything, amazing bathrooms and showers. Karl is one of the most exceptional humans. He is so so kind and accommodating. He was seen only when planned, and Im so happy I had the opportunity to be in his presence as he is such a wonderful, now, friend. Hes lead such a creative and generous life sharing his art of music, meditation, human potential and his high vibrations allover the globe. SO much Yes and Thank you Karl. Im so Happy to have spent time in your lovely home and meeting you!see more

Also consider