Chatham Vacation Rentals, Houses & More


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Areas near Chatham

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1 / 58

Country estate on 100 acres perfect for families

  • 4
  • 6
  • 7 nights min

$1000

Details

Great rentals within 30 miles that match your search

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$286

Details

1 / 8

mile hill b and b

  • 2
  • 4
  • 1 night min

$150

Details

1 / 19

Relax Like Royalty in Your Own Castle!

  • 2
  • 4
  • 1 night min

$299

Details

1
1 / 5

Haddock Hill House

  • 1
  • 2
  • 1 night min

$160

Details

1
1 / 13

Hudson Valley Cottage

  • 1
  • 4
  • 1 night min

$150

Details

2
1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$325

Details

3
1 / 25

Stunning New Construction All SeasonLakefront Home

  • 3
  • 5
  • 7 nights min

$243

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$200

Details

1 / 41

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

  • 6
  • 13
  • 2 nights min

$762

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1700

Details

1 / 48

Total Privacy! Tanglewood Retreat With Berkshire Views!

  • 5
  • 14
  • 2 nights min

$600

Details

1 / 16

Roaring Rapids Cottage

  • 2
  • 5
  • 3 nights min

$250

Details

1 / 28

Country Retreat w/ Pool Near Hip Hudson, NY

  • 3
  • 8
  • 3 nights min

$400

Details

1 / 13

Hillsdale get away

  • 3
  • 10
  • Min stay varies

$150

Details

1 / 19

Relaxing Victorian Farmhouse

  • 3
  • 4
  • 2 nights min

$195

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$92

Details

1
1 / 18

Hillhouse Log Cabin

  • 3
  • 13
  • 2 nights min

$425

Details

1
1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$500

Details

1 / 39

'Bassinova-on-Hudson' Elegant 5BR Estate on the Hudson River w/Infinity Pool

  • 5
  • 12
  • 2 nights min

$1000

Details

1 / 23

Bassinova-on-Hudson

  • 5
  • 10
  • 2 nights min

$2500

Details

1 / 25

Leisure home with beach front property

  • 6
  • 25
  • 2 nights min

$1250

Details

6
1 / 20

Enjoy Summer in The Berkshires. last minute July Dates Available. Great Location

  • 3
  • 8
  • Min stay varies

$275

Details

10
1 / 23

Catskill Mountain/Hudson Valley Lakefront Retreat

  • 2
  • 5
  • 2 nights min

$300

Details

1 / 31

Lakefront house , great lake and mountain views

  • 4
  • 10
  • Min stay varies

$279

Details

2
1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • 2 nights min

$325

Details

30
1 / 20

Berkshire Farmhouse Vacation

  • 5
  • 12
  • Min stay varies

$275

Details

1 / 16

Olde York Farm Distillery Suite

  • 2
  • 6
  • 1 night min

$250

Details

1 / 20

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

  • 3
  • 6
  • 7 nights min

$450

Details

1
1 / 20

Lake Front Paradise

  • 3
  • 10
  • 7 nights min

$300

Details

1
1 / 18

Mussmacher Porch

  • 3
  • 9
  • 1 night min

$125

Details

1 / 6

Dream Guesthouse - Artist's studio, cool country chic

  • 1
  • 4
  • Min stay varies

$185

Details

5
1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$145

Details

1 / 8

Fantastic apt near center of Hudson

  • 2
  • 6
  • 1 night min

$120

Details

1 / 7

Spacious Hudson Getaway

  • 1
  • 6
  • 1 night min

$130

Details

1
1 / 10

Bright Cozy 2BR apt in Hudson

  • 2
  • 6
  • 1 night min

$110

Details

1 / 10

Hudson 2BR with a view

  • 2
  • 6
  • 1 night min

$110

Details

1 / 10

Brand New Construction... clean, clean, clean

  • 3
  • 7
  • 2 nights min

$400

Details

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