Vacation Rentals & House Rentals in Hillsdale

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31 Houses

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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

$488

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 45 minutes

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Price per night from

$230

Great rentals within 20 miles that match your search

The Cottage at Great Falls

Falls Village cottage

2 bedrooms
1 bathroom

sleeps 4

“Perfect getaway location with all the amenities” Perfect getaway location with all the amenities – including a fireplace for a perfect winter stay. The cottage was clean and inviting, and the character of the furnishings and layout were incredible. Whether you want to stay in or venture out to nearby stores and restaurants, the cottage really is a perfect location for a vacation escape.

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$276

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.

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$373

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.

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$299

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.

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$230

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

Catskill finca

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$574

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms
2 bathrooms

sleeps 6

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$153

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms
2 bathrooms

sleeps 5

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$327

Historic Gem Near Hudson, NY

Stuyvesant house

1 bedroom
2 bathrooms

sleeps 3

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Price per night from

$339

Federal house on Armory Square

Hudson house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$1,148

Heart of Lenox

Lenox house

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 1 hour 12 minutes

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Price per night from

$345

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$197

Close to attractions in the Berkshires

South Lee hotel apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$115

A Park View Apartment in Hudson

Hudson apartment

2 bedrooms
1 bathroom

sleeps 4

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$230

Charming Guest Suite

Old Chatham apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$155

Beautiful House in Downtown Hudson, NY

Hudson house

6 bedrooms
3 bathrooms

sleeps 10

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$1,435

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

$804

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom
1 bathroom

sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

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Price per night from

$275