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Old Chatham Rentals

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Old Chatham Rentals

150 Houses

Berkshire Country Estate - The Library Suite

Old Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$171

1 / 21

Beautiful Berkshire Country Estate

Old Chatham house

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$1,028

1 / 24

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$194

1 / 19

nesteldown pet friendly

Old Chatham guest house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$456

1 / 5

Great rentals within 20 miles that match your search

Berkshires Cottage Country Retreat

Stephentown cottage

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$188

1 / 7

2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope

Responds fast! avg. 1 hour 34 minutes

Price per night from

$257

1 / 14

Stunning New Construction All SeasonLakefront Home

Valatie house

3 bedrooms / 3 bathrooms / sleeps 5

“Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go s

Price per night from

$277

1 / 25

Renovated 2 bedroom in Heart of Lenox

Lenox apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$342

1 / 23

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$456

1 / 28

Beautiful House in Downtown Hudson, NY

Hudson house

6 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$798

1 / 18

Beautiful 52 Acre Farmhouse- weekly discounted rates - please inquire.

West Coxsackie house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$285

1 / 43

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$325

1 / 20

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 12

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l

Price per night from

$297

1 / 20

Stunning Home! 120 Acres! Amazing!

Great Barrington house

9 bedrooms / 8 bathrooms / sleeps 16

Price per night from

$4,103

1 / 6

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$166

1 / 16

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$719

1 / 4

Palazzo Hudson: a light filled home BR2

Hudson house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$274

1 / 30

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$428

1 / 12

Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$285

1 / 21

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$114

1 / 9

Leisure home with beach front property

Coxsackie house

6 bedrooms / 3 bathrooms / sleeps 25

Price per night from

$1,767

1 / 25

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 29 minutes

Price per night from

$114

1 / 8

Bright and Airy 2BR near the center

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$149

1 / 16

Red Mapple Farm

Malden Bridge house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$502

1 / 10

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$215

1 / 18

Troy, NY - Collar City Hideaway

Troy apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 32 minutes

Price per night from

$74

1 / 15

Cozy basement Studio Apartment Albany,NY

Albany house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$102

1 / 15

Blue SKies

Hudson apartment

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$285

1 / 20

Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$257

1 / 12

Double Room in Historic Farmhouse

West Coxsackie b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$114

1 / 13

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$171

1 / 4

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$342

1 / 31

Berkshire Getaway at 'Tofu'S Retreat'

Alford chateau

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

Price per night from

$245

1 / 22

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$114

1 / 13

Newly Renovated Apartment in Heart of Hudson

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$228

1 / 7

Palazzo Hudson: a light filled home BR3

Hudson house

1 bedroom / 2 bathrooms / sleeps 3

Price per night from

$274

1 / 30

Gracious 3-BR Garden Apt. in the Heart of Hudson

Hudson apartment

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$285

1 / 18

Berkshire House Share-The Blue Room

Lee house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$86

1 / 10
Viewing 38 of 150
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