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Monterey Rentals

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83 Houses

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Monterey cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 44 minutes

Price per night from

$131

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

Monterey cottage

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 12 minutes

Price per night from

$241

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$568

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$508

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$231

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

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 12 minutes

Price per night from

$237

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 12 minutes

Price per night from

$242

Great rentals within 20 miles that match your search

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$193

Riverwood - Cozy Carriage House in the Woods

Falls Village apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$290

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$773

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$129

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$921

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$194

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$233

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,227

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$181

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.

Price per night from

$284

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$259

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$158

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$212

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$911

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$441

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$288

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.

Responds fast! avg. 6 minutes

Price per night from

$216

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$841

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$317

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

$227

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$312

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$165

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

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$115

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$217

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

$343

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$515

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 9 minutes

Price per night from

$229

Tentrr Signature Site - Maple Corner Farm

Blandford tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$156

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

Chesterfield tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$149

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rentals in Monterey

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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

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