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Hillsdale Rentals

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100 Houses

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

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,230

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

$230

Tentrr Signature Site - Hillsdale Hideaway

Hillsdale tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$163

Great rentals within 20 miles that match your search

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,576

The Artist's House - Special Winter Rates!

Hudson house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$453

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$232

(FAKE - DO NOT BOOK THIS) Sleek, Modern Apartment - Steps from Hudson River

Athens apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$143

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$924

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

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,294

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

Stunning New Construction All SeasonLakefront Home

Valatie house

3 bedrooms / 3 bathrooms / sleeps 5

“Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go swimming in it, however, but it's so murky you can't see your thighs in the water, much less the bottom. Our twenty-something son wanted to swim across it, and I kept thinking, if he goes under you'd never see him. As it was, he did swim across and we followed in a row boat. We would definitely return were it not for the lake.

Price per night from

$305

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$181

Bellavista Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$205

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$260

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

$213

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$913

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$602

Mrs. Pleasant’s Plant Based B + B

Athens house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$194

Historic Gem Near Hudson, NY

Stuyvesant house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$352

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

$442

Lakefront Home w/ Kayaks, Peddle Boat & Dock!

Elizaville house

2 bedrooms / 2 bathrooms / sleeps 2

Responds fast! avg. 1 hour 5 minutes

Price per night from

$111

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 14 minutes

Price per night from

$173

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

$289

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 46 minutes

Price per night from

$683

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$570

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

$844

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$318

Brook Hill Farm House

Valatie house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$372

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

Catskill finca

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 12 minutes

Price per night from

$569

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$509

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

$228

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