Monterey Rentals

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98 Houses

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

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$489

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 48 minutes

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$458

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

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 26 minutes

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$212

NEW! Monterey Home w/Porch by Beach & State Parks!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 2 hours 26 minutes

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$229

Best vacation home in Berkshires (Summer & rest of seasons ..1, 2 or 3 families)

Monterey house

6 bedrooms / 5 bathrooms / sleeps 10

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$749

Best Vacation Home in Berkshires..(Winter & rest of seasons 1, 2, or 3 families)

Monterey house

6 bedrooms / 5 bathrooms / sleeps 10

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$745

Great rentals within 20 miles that match your search

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“Incredible vacation stay or seasonal rental” My family rented this home for an entire summer. The house is beautiful and perfectly suited for any sized family. We stayed with two adults and three children (infant-7yrs old), but also had several occasions with overnight guests. Three bedrooms are upstairs, leaving one/two rooms downstairs that functioned as a guest area. It was a perfect scenario with one of the two full bathrooms downstairs, our guests had full privacy. The house is very well kept, comfortable furniture, modern kitchen, and gorgeous views from the 50+ windows! The back yard is huge and our children spent many hours running around and playing freely. We were very pleased with the quietness and safety of the neighborhood. West Stockbridge is a prime and central location for all of the Berkshire's attractions. We have rented seasonal homes in the Berkshires for eleven years and this has been our best experience, by far. The homeowners are extremely welcoming and accommodating, making sure we were comfortable during our stay. We highly recommend this property!

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$407

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

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$436

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

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$329

Berkshire Getaway at 'Tofu'S Retreat'

Alford chateau

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

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$248

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 24 minutes

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$260

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

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$144

Historic Huntington Home - Walk to Westfield River

Huntington house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 24 minutes

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$219

4 Bedroom Furnished House in Lakeville Connecticut

Lakeville house

4 bedrooms / 3 bathrooms / sleeps 8

“Excellent location, great experience.” The owner, Paul, is very friendly and showed us around as soon as we got there. The house is spacious, clean, and has everything you will need for your stay. Wifi, washer/drier, gas grill, dishwasher, and a lot of small things you would have in your own home. A lake with boat rental, small basketball court, and charcoal grills is only 3-5 minute walking! If you like being outside - that's the place to be. A pizza restaurant, bar, and a coffee / sandwich shops are right around the corner - 1 minute walk, if that. Wine / beer / liquor store is a 5 minute walk - that was a nice surprise as we like to try local wines. If you are there for any kind of racing, Lime Rock Park is only 5 miles away. That was one of the biggest benefits for us - extremely convenient. Not sure how to make this not sound like a sales pitch, but we had a great time, no issues, and will absolutely come again.

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$375

House share/room for rent

Lee private room

1 bedroom / 1 bathroom / sleeps 1

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$77

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

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$172

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“the cottage description is a perfect fit "romantic getaway in id” We have stayed in many B&B;'s and cottage rentals on the east coast...this experience was one of the best! The owners are exceptional hosts and the accommodations are just as described...even better. The setting in the berkshires is fabulous and the location is a perfect location for touring the area (western ma and the Hudson valley). The hosts provide ample information about great restaurants and lovely walks/hikes in the area. We are already planning our next trip to the cottage!

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$228

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

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$516

Renovated 2 bedroom in Heart of Lenox

Lenox apartment

2 bedrooms / 1 bathroom / sleeps 4

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$344

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Handy, convenient, comfortable, well equipped and peaceful rental in terrific location.” In some rentals, you have to bring literally everything. This place was just the opposite. Great linens provided, napkins, paper towels and toilet paper and various necessities for cooking. Very roomy with 4 bedrooms and 5 beds, a good shower, hair dryer, washer dryer, good seating in the living room. Good lighting in the bedrooms, so appreciated. Convenient parking, walking distance to the town of Lenox with shops and restaurants at hand. Hope i have the chance to come back.

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$229

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

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$153

|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 1 hour 21 minutes

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$516

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

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$172

RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

“Beautiful spot in the Berkshires” My husband and I stayed here while I was singing nearby in a concert of Berkshire Choral International. We loved the location out in the country, with beautiful views of pastures, forests, and the Berkshires in the background. The grounds are lovely, and the basement apartment where we stayed was quiet and comfortable. We only regretted that we couldn't stay longer.

Responds fast! avg. 12 minutes

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$217

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

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$201

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$264

Great Vacation House in the Berkshires by Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

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$213

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

“October in Berkshires” Great location near major attractions such as Tanglewood. Screened porch is great for pre dinner get together. Old house but well maintained except for old house smell. Plenty of room for 6 people.

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$298

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$241

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

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$216

Rustic Berkshires Cottage, Steps to Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 26 minutes

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$126

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

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Price per night from

$212

Private Berkshire Estate w/Pool & Tennis Court

Great Barrington house

4 bedrooms / 4 bathrooms / sleeps 12

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$659

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$287

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

Richmond house

3 bedrooms / 3 bathrooms / sleeps 6

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$573

Stunning Home! 120 Acres! Amazing!

Great Barrington house

9 bedrooms / 8 bathrooms / sleeps 16

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$4,122

3BR Lee House w/ Easy Access to Main Street!

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$275

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

“Great family accommodations in the Berkshires” We needed a house for our family of five, plus my brother, one daughter in law and a girl friend that provided space and privacy - for a summer weekend in the Berkshires. This property filled the bill admirably. It's a rambling farmhouse with lots of rooms, a well-appointed kitchen, and great outdoor space - perfect for our group. The location is very convenient as well, with easy access to all of the towns in Southern Berkshire County. The owners were responsive and very easy to deal with, they even left a nice welcome basket with local food items for us. Would definitely rent this property again.

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$373

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rentals in Monterey

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