Monterey Rentals

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Filtering by: Horse riding

30 Houses

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

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$212

Great rentals within 20 miles that match your search

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

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

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Price per night from

$263

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$172

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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Price per night from

$372

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$245

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

“Clean, attention to detail, everything is updated, fantastic deck, wonderful views.” Loved being so close to Jacob's Pillow and great restaurants (Xochil, Gedney Farm, Dream Away Lodge). Visiting MOCA and the Norman Rockwell were also a wonderful treat. Early dawn and dusk were wonderful at the cottage with daily visits from a bald eagle flying right in front of the deck. Perfect for a restful vacation.

Responds fast! avg. 18 minutes

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Price per night from

$206

|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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Price per night from

$514

Responds fast! avg. 2 hours 3 minutes

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Price per night from

$912

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$152

Overnight at Althouse -Higgins

Hillsdale apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$200

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$240

Rustic Berkshires Cottage, Steps to Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$126

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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Price per night from

$297

Berkshire House Share-The Blue Room

Lee house

3 bedrooms / 1 bathroom / sleeps 2

“Nice landlord, great kitchen, comfortable room” This is an excellent budget-friendly option for a visit to the Berkshires. By preparing and eating all my meals in the shared kitchen, I saved plenty during my 10-day stay. Lee is a lovely town in its own right, and you're minutes from other Berkshire destinations. Robin, the landlord, is super friendly, as is her cat. NB: no alcohol permitted.

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Price per night from

$86

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

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Price per night from

$815

'Butterfly Hill' West Stockbridge Home on 3 Acres!

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$189

Luxury Becket Home on 11 Acres W/ Swimming Pond!

Becket house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$373

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$212

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Otis log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$115

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$241

NEW! Charming Berkshires Cottage on Ashmere Lake

Hinsdale cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$224

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.

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Price per night from

$487

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$516

Zen Cottage in the Woods

Great Barrington house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$229

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

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

$401

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$327

3BD Newly Rennovated Contempoary Near Stockbridge

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$344

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

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$1,374

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