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Chatham Rentals

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Price range

Per night

$10 - $500

Rental types

Chatham Rentals

140 Houses

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,006

1 / 58

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

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Country Artists residence Near Hudson, NY

Stuyvesant house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 29 minutes

Price per night from

$165

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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

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Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$302

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Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$216

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Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,207

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Lakefront house , great lake and mountain views

Athens house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$315

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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

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"The Barn" on Tower Mountain

Hancock house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$151

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Newly remodeled scandi 2BR apt with backyard

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$121

1 / 13

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

Cabin on the Poetic Creek

Leeds log cabin

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$136

1 / 10

Escape to Avalon Cottage in the Hudson Valley

Craryville house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$146

1 / 16

320 Union

Hudson apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$166

1 / 12

INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 59 minutes

Price per night from

$181

1 / 30

RIVERSONG "PENTHOUSE"

North Egremont room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 35 minutes

Price per night from

$140

1 / 32

Leisure home with beach front property

Coxsackie house

6 bedrooms / 3 bathrooms / sleeps 25

Price per night from

$1,559

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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

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$151

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Berkshire House Share-The Blue Room

Lee house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$76

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Bassinova-on-Hudson

Coxsackie villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$2,515

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Palazzo Hudson: a light filled home BR3

Hudson house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$242

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Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$170

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Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$151

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Nasturtium Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$151

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Beautifully Renovated Berkshires Farmhouse

West Stockbridge b and b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$212

1 / 16

The Barn at Copake Lake

Craryville barn

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$603

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Brook Hill Farm House

Valatie house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$331

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Private Berkshire Estate w/Pool & Tennis Court

Great Barrington house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$575

1 / 21

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

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1 Bedroom Hudson Valley Farm House

Craryville guest house

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$322

1 / 18

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$134

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Hudson Valley Farm House

Craryville house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$322

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