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Old Chatham Rentals

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Old Chatham Rentals

179 Houses

Berkshire Country Estate - The Library Suite

Old Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$150

1 / 21

Beautiful Berkshire Country Estate

Old Chatham house

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$900

1 / 24

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$170

1 / 19

nesteldown pet friendly

Old Chatham guest house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$400

1 / 5

Great rentals within 20 miles that match your search

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$252

1 / 5

Country Artists residence Near Hudson, NY

Stuyvesant house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 29 minutes

Price per night from

$165

1 / 14

3BR Lee House w/ Easy Access to Main Street!

Lee house

1 bedroom / 2 bathrooms / sleeps 10

Responds fast! avg. 9 minutes

Price per night from

$240

1 / 24

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,207

1 / 29

Lakefront house , great lake and mountain views

Athens house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$315

1 / 31

Idyllic Berkshire Home perfect for families or friends with pool and gardens

Richmond house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$504

1 / 12

"The Barn" on Tower Mountain

Hancock house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$151

1 / 7

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$101

1 / 26

Bright and Airy 2BR near the center

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$131

1 / 16

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$378

1 / 24

mile hill b and b

Kinderhook house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$186

1 / 8

Mussmacher Porch

Hudson apartment

3 bedrooms / 1 bathroom / sleeps 9

Responds fast! avg. 47 minutes

Price per night from

$126

1 / 18

1876 Center Square Brownstone

Albany house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$176

1 / 9

RIVERSONG "PENTHOUSE"

North Egremont room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 35 minutes

Price per night from

$140

1 / 32

Jiminy Peak Luxury Ski In/Ski Out Home

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$392

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$221

1 / 13

Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)

Stockbridge cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 13 minutes

Price per night from

$301

1 / 17

Relaxing Victorian Farmhouse

Philmont house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$197

1 / 19

Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$225

1 / 12

Washington Park Inn - Urban Inn on the park near Hospital & Center Sq w/ Parking

Albany b and b

7 bedrooms / 7 bathrooms / sleeps 17

Price per night from

$130

1 / 11

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 17 minutes

Price per night from

$176

1 / 10

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$130

1 / 23

Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$458

1 / 10

Palazzo Hudson: a light filled home BR1

Hudson house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$242

1 / 30

Troy, NY - Collar City Hideaway

Troy apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 8 minutes

Price per night from

$66

1 / 15

Bassinova-on-Hudson

Coxsackie villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$2,515

1 / 23

Cozy basement Studio Apartment Albany,NY

Albany house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$90

1 / 15

Palazzo Hudson: a light filled home BR3

Hudson house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$242

1 / 30

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b and b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$212

1 / 16

Brook Hill Farm House

Valatie house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$331

1 / 19

Private Berkshire Estate w/Pool & Tennis Court

Great Barrington house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$575

1 / 21

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$202

1 / 8

Perfect for skiers in the Berkshires

Lee townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$118

1 / 14

Bright and Spacious Apt sleeps up to 4

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$136

1 / 12
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