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Monterey Rentals

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88 Results

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88 Houses

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Monterey cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$173

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

Monterey cottage

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 59 minutes

Price per night from

$288

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$579

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$518

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$235

Renovated Lakefront House w/ Dock: Pets Welcome!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 59 minutes

Price per night from

$827

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 59 minutes

Price per night from

$243

Great rentals within 20 miles that match your search

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$196

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$784

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$934

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$197

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$174

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,244

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$183

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$263

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$923

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

$447

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$322

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

$266

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$202

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$197

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 55 minutes

Price per night from

$161

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$231

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

$298

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

$230

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 25 minutes

Price per night from

$863

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

$375

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$571

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are beautiful. Thank you!

Price per night from

$343

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$315

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

$171

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$516

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

$251

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$218

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$287

Spacious Contemporary With Beautiful Gardens

Housatonic house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$267

Private Guest House in Dtwn Lenox, Walk to Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 59 minutes

Price per night from

$252

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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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