Hillsdale Homes, Condos & More


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Areas near Hillsdale

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1
1 / 18

Hillhouse Log Cabin

  • 3
  • 13
  • 2 nights min

$425

Details

14
1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$175

Details

3
1 / 11

Overnight at Althouse -Higgins

  • 2
  • 4
  • 2 nights min

$175

Details

1 / 13

Hillsdale get away

  • 3
  • 10
  • Min stay varies

$150

Details

1 / 48

Total Privacy! Tanglewood Retreat With Berkshire Views!

  • 5
  • 14
  • 2 nights min

$600

Details

Great rentals within 30 miles that match your search

1 / 15

S. Berkshires Mountain Treehouse • Views • Privacy

  • 2
  • 4
  • 3 nights min

$375

Details

1 / 15

Newly Renovated Vacation Home near Catamount Ski

  • 3
  • 10
  • Min stay varies

$299

Details

1
1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$375

Details

1 / 11

Beautiful Cottage at the foot of the Berkshires

  • 2
  • 4
  • 2 nights min

$175

Details

2
1 / 27

Copake Lakeview Ranch

  • 3
  • 12
  • Min stay varies

$189

Details

8
1 / 15

Outdoor getaway hunting,fishing,skiing..relaxation

  • 3
  • 9
  • 2 nights min

$191

Details

1
1 / 14

Newly Renovated Lakefront Getaway on Robinson Pond

  • 3
  • 6
  • 3 nights min

$200

Details

1
1 / 4

Cozy Copake Lake Cottage

  • 3
  • 6
  • 7 nights min

$108

Details

1 / 10

Ranch House in Lakeside Community

  • 3
  • 6
  • 2 nights min

$200

Details

1 / 20

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

10
1 / 55

RiverSong Suite In The Berkshires

  • 1
  • 2
  • 1 night min

$189

Details

4
1 / 16

TAKE ME HOME, COUNTRY ROADS

  • 3
  • 6
  • 4 nights min

$225

Details

21
1 / 13

Berkshires: Romantic Cottage with spectacular view

  • 1
  • 3
  • Min stay varies

$189

Details

5
1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$145

Details

1 / 19

Relaxing Victorian Farmhouse

  • 3
  • 4
  • 2 nights min

$195

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1700

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$200

Details

1
1 / 10

Cozy and clean in Gt Barrington- 1 week in summer!

  • 2
  • 4
  • 3 nights min

$195

Details

1
1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$500

Details

1 / 6

Stunning Home! 120 Acres! Amazing!

  • 9
  • 16
  • 3 nights min

$3600

Details

3
1 / 30

Gem of the Berkshires, walk to downtown & lake.

  • 5
  • 12
  • 2 nights min

$400

Details

1 / 18

Restored 1940s Cabin 30 Mile Views

  • 2
  • 5
  • 2 nights min

$250

Details

2
1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$188

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$650

Details

1 / 25

NEW! Charming 3BR Great Barrington House by River!

  • 3
  • 8
  • Min stay varies

$205

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$450

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

$1500

Details

1 / 41

Charming B&B sud Luberon in Vineyards, with a Pool and Balcony

  • 6
  • 13
  • 2 nights min

$762

Details

1 / 30

Evergreen Pines Country Estate Villa

  • 4
  • 8
  • 1 night min

$2000

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$286

Details

1 / 16

Olde York Farm Distillery Suite

  • 2
  • 6
  • 1 night min

$250

Details

1 / 16

Beautifully Renovated Berkshires Farmhouse

  • 2
  • 4
  • 2 nights min

$210

Details

1 / 28

Country Retreat w/ Pool Near Hip Hudson, NY

  • 3
  • 8
  • 3 nights min

$400

Details

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