Stephentown Vacation Rentals, Houses & More


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Areas near Stephentown

Great rentals within 20 miles that match your search

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 18

Troy, NY - Elegant Emma Willard

  • 2
  • 5
  • 2 nights min

$110

Details

1 / 5

Berkshire Mountain Lodge - Fri, Sat,Sun check ins only! Inbox x

  • 1
  • 4
  • 7 nights min

$157

Details

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$172

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 12

Heart of the Berkshires!

  • 3
  • 6
  • 2 nights min

$226

Details

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

1 / 4

Golden Triangle in the Berkshires

  • 2
  • 4
  • 2 nights min

$2500

Details

1 / 49

Romantic Lakefront Mountain Hideaway

  • 3
  • 8
  • 1 night min

$248

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$61

Details

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$71

Details

1 / 16

Family-friendly Cottage Near Lake, Tanglewood

  • 3
  • 7
  • Min stay varies

$285

Details

1 / 16

Luxury Fox Hollow Laurel Lake Ranch

  • 4
  • 11
  • Min stay varies

$501

Details

1 / 19

Wyndham Bentley Brook

  • 2
  • 8
  • 2 nights min

$201

Details

1 / 10

Heart of Lenox

  • 2
  • 4
  • Min stay varies

$176

Details

1 / 6

Retreat in the Woods

  • 2
  • 4
  • 2 nights min

$201

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$93

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$231

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 24

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$196

Details

1 / 31

3 BR apartment, walking distance to Mass MoCa

  • 3
  • 15
  • Min stay varies

$166

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 23

Apartment walking distance to Mass MoCa!!

  • 2
  • 10
  • Min stay varies

$155

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

Details

1 / 17

House On Main Street

  • 4
  • 16
  • Min stay varies

$445

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 7

Berkshires Cottage Country Retreat

  • 3
  • 6
  • 2 nights min

$166

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$630

Details

1 / 25

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

  • 4
  • 10
  • 2 nights min

$401

Details

1 / 12

Ski Cottage in the Berkshire Hills

  • 3
  • 6
  • 3 nights min

$250

Details

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