Old Chatham Vacation Rentals, Houses & More


1 - 38 of 146

View larger map

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 / 10

Berkshire House Share-The Blue Room

  • 3
  • 2
  • 1 night min

$76

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

1 / 47

Jacob's Tanglewood Ranch (great for groups 10+)

  • 5
  • 20
  • Min stay varies

$1000

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

1 / 18

Mussmacher Porch

  • 3
  • 9
  • 1 night min

$125

Details

1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$61

Details

1 / 9

The Artist's House - Special Winter Rates!

  • 3
  • 6
  • 2 nights min

$351

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$93

Details

1 / 55

RiverSong Suite In The Berkshires

  • 1
  • 2
  • 1 night min

$190

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$475

Details

1 / 5

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

  • 1
  • 4
  • 7 nights min

$157

Details

1 / 10

Hudson 2BR with a view

  • 2
  • 6
  • 1 night min

$110

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 13

Hudson Valley Cottage

  • 1
  • 4
  • 1 night min

$150

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights 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 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$231

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$176

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 / 15

Newly Renovated Vacation Home near Catamount Ski

  • 3
  • 10
  • Min stay varies

$300

Details

1 / 7

Spacious Hudson Getaway

  • 1
  • 6
  • 1 night min

$130

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$134

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

Details

1 / 13

Berkshires: Romantic Cottage with spectacular view

  • 1
  • 3
  • Min stay varies

$226

Details

1 / 20

Blue SKies

  • 3
  • 7
  • 2 nights min

$250

Details

1 / 28

Country Retreat w/ Pool Near Hip Hudson, NY

  • 3
  • 8
  • 3 nights min

$401

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