Chatham Vacation Rentals, Houses & More


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Areas near Chatham

1 / 58

Country estate on 100 acres perfect for families

  • 4
  • 6
  • 7 nights min

$1001

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Great rentals within 20 miles that match your search

1 / 16

TAKE ME HOME, COUNTRY ROADS

  • 3
  • 6
  • 4 nights min

Inquire for Rates

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1 / 20

Lake Front Paradise

  • 3
  • 10
  • 7 nights min

$300

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$130

Details

1 / 55

RiverSong Suite In The Berkshires

  • 1
  • 2
  • 1 night min

$190

Details

1 / 16

Luxury Fox Hollow Laurel Lake Ranch

  • 4
  • 11
  • Min stay varies

$500

Details

1 / 6

Stunning Home! 120 Acres! Amazing!

  • 9
  • 16
  • 3 nights min

$3601

Details

1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$175

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$325

Details

1 / 19

Relaxing Victorian Farmhouse

  • 3
  • 4
  • 2 nights min

$195

Details

1 / 26

3BD Newly Rennovated Contempoary Near Stockbridge

  • 3
  • 6
  • 3 nights min

$300

Details

1 / 25

Stunning New Construction All SeasonLakefront Home

  • 3
  • 5
  • 7 nights min

$243

Details

1 / 54

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

  • 4
  • 10
  • 1 night min

$400

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$650

Details

1 / 41

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

  • 6
  • 13
  • 2 nights min

$769

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 6

Rustic Rivers end room in the barn at chestnut lodge

  • 1
  • 4
  • 2 nights min

$156

Details

1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$126

Details

1 / 9

The Artist's House - Special Winter Rates!

  • 3
  • 6
  • 2 nights min

$351

Details

1 / 10

Cabin on the Poetic Creek

  • 1
  • 4
  • 1 night min

$135

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$230

Details

1 / 13

Hudson Valley Cottage

  • 1
  • 4
  • 1 night min

$151

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$151

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 28

Country Retreat w/ Pool Near Hip Hudson, NY

  • 3
  • 8
  • 3 nights min

$400

Details

1 / 10

Brand New Construction... clean, clean, clean

  • 3
  • 7
  • 2 nights min

$400

Details

1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$143

Details

1 / 7

Berkshires Cottage Country Retreat

  • 3
  • 6
  • 2 nights min

$165

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$151

Details

1 / 12

320 Union

  • 2
  • 4
  • 2 nights min

$165

Details

1 / 7

Newly Renovated Apartment in Heart of Hudson

  • 2
  • 4
  • Min stay varies

$200

Details

1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$188

Details

1 / 16

Olde York Farm Distillery Suite

  • 2
  • 6
  • 1 night min

$251

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$200

Details

1 / 19

Lake House

  • 5
  • 9
  • 7 nights min

$715

Details

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$173

Details

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$151

Details

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