Stephentown Vacation Rentals, Houses & More


1 - 4 of 4

View larger map

Areas near Stephentown

Don't let other travelers get your favorite vacation rental. You're so close to securing your perfect getaway. Book today.

6
1 / 25

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

  • 4
  • 10
  • 2 nights min

$400

Details

1 / 7

Berkshires Cottage Country Retreat

  • 3
  • 6
  • 2 nights min

$165

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$600

Details

1 / 12

Ski Cottage in the Berkshire Hills

  • 3
  • 6
  • 3 nights min

$250

Details

Great rentals within 30 miles that match your search

2
1 / 16

PanoramicView1000 sq ft Guest Quarters Berkshires

  • 1
  • 6
  • 2 nights min

$145

Details

1 / 13

Berkshires Summer Rental Beaver Pond Hancock MA

  • 3
  • 6
  • 30 nights min

$250

Details

1
1 / 4

Golden Triangle in the Berkshires

  • 2
  • 4
  • 2 nights min

$2500

Details

1 / 17

Whitman Woods: Private Berkshire Vacation, 4 acre

  • 4
  • 8
  • 1 night min

$100

Details

3
1 / 14

2200sf Country House on 16 Acres-2 Miles to Jiminy

  • 4
  • 9
  • 2 nights min

$225

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$200

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$175

Details

1 / 10

Vacation Village in the Berkshires Available July 22-29

  • 2
  • 8
  • 7 nights min

$158

Details

1 / 7

Vacation Village in the Berkshires - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$157

Details

1 / 26

Dazzling 2BR Hancock Condo W/Private Deck, Charcoal Grill & Gorgeous Mountain

  • 2
  • 6
  • Min stay varies

$185

Details

1 / 6

Jiminy Peak Ski Resort-Country Village's Best Unit

  • 2
  • 6
  • 1 night min

$250

Details

9
1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$66

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 13

Jiminy Peak Luxury Ski In/Ski Out Home

  • 3
  • 8
  • Min stay varies

$329

Details

2
1 / 16

Berkshires Vacation Rental - Bentley Brook Resort Suite

  • 2
  • 6
  • 3 nights min

$199

Details

2
1 / 19

Wyndham Bentley Brook

  • 2
  • 8
  • 2 nights min

$200

Details

1
1 / 8

Wyndham Bentley Brook - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$258

Details

1 / 23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

  • 2
  • 6
  • 2 nights min

$199

Details

1 / 24

Vacation Village in the Berkshires

  • 2
  • 8
  • 7 nights min

$129

Details

1 / 49

Romantic Lakefront Mountain Hideaway

  • 3
  • 8
  • 1 night min

$247

Details

15
1 / 10

Stone School Cottage

  • 2
  • 5
  • 2 nights min

$155

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

1 / 19

Charming Berkshires lakefront house, great views

  • 2
  • 5
  • 2 nights min

$200

Details

1 / 25

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$195

Details

3
1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

1 / 17

House On Main Street

  • 4
  • 16
  • Min stay varies

$446

Details

8
1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1
1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 6 nights min

$200

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$92

Details

2
1 / 5

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

  • 1
  • 4
  • 7 nights min

$158

Details

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

1
1 / 5

Haddock Hill House

  • 1
  • 2
  • 1 night min

$160

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more