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Hillsdale Rentals

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154 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

$495

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$708

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 54 minutes

Price per night from

$202

Overnight at Althouse -Higgins

Hillsdale apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$207

Tentrr Signature - Hillsdale Hideaway

Hillsdale tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$160

Great rentals within 20 miles that match your search

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$532

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$591

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$177

New Private Hudson 1BR

Hudson apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$141

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,349

Price per night from

$699

Lakefront house , great lake and mountain views

Athens house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 3 minutes

Price per night from

$368

Charming Farmhouse on Magical 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$464

Bright and Airy 2BR near the center

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$153

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$177

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$589

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.

Price per night from

$354

Blue SKies

Hudson apartment

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$295

Guest House on a Trout River w/ Year Round Hot Tub

Red Hook house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$206

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$201

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$177

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$471

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$248

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$530

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$206

Fantastic apt near center of Hudson

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$142

4 Bedroom Furnished House in Lakeville Connecticut

Lakeville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$383

Turning Point - Family Retreat & Group Getaway

Great Barrington house

7 bedrooms / 8 bathrooms / sleeps 15

Price per night from

$944

Bright Cozy 2BR apt in Hudson

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$130

2 Bedroom Hudson Valley Farm House

Craryville guest house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$378

1 Bedroom Hudson Valley Farm House

Craryville guest house

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$378

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$504

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$177

4 Bedroom Hudson Valley Farm House

Craryville guest house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$378

Charming Private Guest Suite in Historic Village in the Berkshires

New Marlborough studio

Studio / 1 bathroom / sleeps 2

Price per night from

$112

Hudson 2BR with a view

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$130

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

$236

Modern cabin in the woods + year round heated pool

Red Hook house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$284

Viewing 38 of 154
rentals in Hillsdale

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