Old Chatham Vacation Rentals, Houses & More


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Areas near Old Chatham

1 / 5

nesteldown pet friendly

  • 4
  • 8
  • 5 nights min

$401

Details

Great rentals within 20 miles that match your search

1 / 18

Hillhouse Log Cabin

  • 3
  • 13
  • 2 nights min

$425

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 11

Berkshires Spacious Comfortable Charming Farmhouse

  • 3
  • 8
  • 2 nights min

$300

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

1 / 12

little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 23

Catskill Mountain/Hudson Valley Lakefront Retreat

  • 2
  • 5
  • 2 nights min

$300

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$67

Details

1 / 25

Leisure home with beach front property

  • 6
  • 25
  • 2 nights min

$1250

Details

1 / 18

Mussmacher Porch

  • 3
  • 9
  • 1 night min

$125

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$61

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$93

Details

1 / 8

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

  • 2
  • 6
  • 7 nights min

$258

Details

1 / 20

Lake Front Paradise

  • 3
  • 10
  • 7 nights min

$300

Details

1 / 13

Double Room in Historic Farmhouse

  • 1
  • 2
  • 1 night min

$100

Details

1 / 20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

  • 3
  • 6
  • 7 nights min

$501

Details

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 1 night min

$176

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

1 / 25

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

  • 4
  • 10
  • 2 nights min

$401

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$630

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 5

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

  • 1
  • 4
  • 7 nights min

$157

Details

1 / 18

Gracious 3-BR Garden Apt. in the Heart of Hudson

  • 3
  • 6
  • 2 nights min

$250

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$172

Details

1 / 31

Lakefront house , great lake and mountain views

  • 4
  • 10
  • Min stay varies

$310

Details

1 / 25

Stunning New Construction All SeasonLakefront Home

  • 3
  • 5
  • 7 nights min

$243

Details

1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$145

Details

1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$144

Details

1 / 9

2 room office +wc with 1 bedroom , kitchen +bathr.

  • 1
  • 2
  • 3 nights min

$72

Details

1 / 10

Vacation Village in the Berkshires Available July 22-29

  • 2
  • 8
  • 7 nights min

$157

Details

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

1 / 20

Berkshire Farmhouse Vacation

  • 5
  • 12
  • Min stay varies

$275

Details

1 / 48

Total Privacy! Tanglewood Retreat With Berkshire Views!

  • 5
  • 14
  • 2 nights min

$600

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

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