Monterey Rentals

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Filtering by: Balcony or terrace

25 Houses

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$489

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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Price per night from

$212

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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Price per night from

$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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Price per night from

$436

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

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Price per night from

$227

The Cottage at Great Falls

Falls Village cottage

2 bedrooms / 1 bathroom / sleeps 4

“Lovely” My husband and I stayed here for a recent visit on a trip to New England. We chose this Falls Village cottage and it was truly wonderful. Everything from the location, right up against the Housatonic river, to the beautiful care that has so clearly gone into this cottage, we couldn't have been happier with our choice. The pictures we saw before we arrived gave us a good idea about the cottage but they just can't do it justice as once you arrive you begin to see everything about this special place that makes it so unique.

Responds fast! avg. 50 minutes

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Price per night from

$277

Outdoor getaway hunting,fishing,skiing..relaxation

Copake house

3 bedrooms / 2 bathrooms / sleeps 9

“Perfect Wkd Getaway” I was looking for a quaint, neat and comfortable place to stay while in the are for my cousin's wedding and I found the perfect place. More spacious than it appears in pictures, the kitchen and livingroom and bedrooms were a good size. I wish we had had more time to spend on the deck in back or the fire pit, but it was just too much craziness packed in!! The front porch actually wraps around to the back and is super nice for coffee in the morning or a glass of wine in the evening. The neighborhood was quiet with super nice neighbors- and the walk to the nearby lake (we didn't have time to take advantage of the car passes that were provided to use for the small beach at the lake) was refreshing. This place is close to the town of Copake and in the perfect spot- I am so glad I found it and will definitely keep in mind and share it for the future!!! The owners were a phone all away and answered any questions promptly. Thanks again!!!

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Price per night from

$219

Country Victorian Serenity in the Berkshires

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$263

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$802

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$516

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful weekend in a wonderful home in Great Barrington” We are a group of 10 that gather from Mass./N.Y./ New Jersey every summer to enjoy all that the Berkshires have to offer. We came upon this gem and could not have been happier. The homeowners are a wonderful couple who take great pride in their home and this comes through in the way the place is appointed and artwork dispersed throughout the house.Yes, the house is a short walk to both town and the lake but truthfully sitting on the deck overlooking the mountains will keep you planted in one spot. Having your morning coffee overlooking the fog covered hills was a wonderful way to start your day.Neither the description nor the photos do this home justice, no question you will be pleased with your choice

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Price per night from

$344

Best vacation home in Berkshires: Summers & Winters best for 1, 2 or 3 families

Great Barrington villa

6 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$785

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$1,374

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$115

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$166

Responds fast! avg. 1 hour 45 minutes

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Price per night from

$915

Berkshire Getaway Home with Lake Access

Otis house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 4 minutes

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Price per night from

$453

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$258

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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Price per night from

$217

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$126

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$453

NEW LISTING SPECIAL: 10% off! Captivating Home Overlooking Stevens Lake!

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$516

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

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Price per night from

$818

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$241

Stunning Home! 120 Acres! Amazing!

Great Barrington house

9 bedrooms / 8 bathrooms / sleeps 16

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Price per night from

$4,122

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