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Stephentown Rentals

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Price range

Per night

$10 - $500

Stephentown Rentals

140 Houses

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$631

1 / 4

Berkshires Cottage Country Retreat

Stephentown cottage

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$166

1 / 7

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 29 minutes

Price per night from

$376

1 / 23

Ski Cottage in the Berkshire Hills

Stephentown house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$251

1 / 12

Great rentals within 20 miles that match your search

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$301

1 / 31

Mountain Views Atop Blueberry Hill on 40 Acres

Austerlitz house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$201

1 / 18

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$326

1 / 10

Beautiful Vacation Home on a Private Lake

Petersburg house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$215

1 / 6

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,202

1 / 29

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

Richmond house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$501

1 / 12

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,

Price per night from

$201

1 / 21

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$101

1 / 8

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

Price per night from

$186

1 / 37

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

Price per night from

$196

1 / 31

Jiminy Peak Luxury Ski In/Ski Out Home

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$390

1 / 13

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms / 2 bathrooms / sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

Price per night from

$301

1 / 12

Price per night from

$226

1 / 28

Beautiful Berkshire Country Estate

Old Chatham house

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$902

1 / 24

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

$261

1 / 20

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

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$101

1 / 13

Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$251

1 / 21

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$456

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

Renovated 2 bedroom in Heart of Lenox

Lenox apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$301

1 / 23

chestnut lodge Queens Room

Lee b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 45 minutes

Price per night from

$146

1 / 2

Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Adams house

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$401

1 / 38

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,002

1 / 58

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$176

1 / 13

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$151

1 / 4

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

$216

1 / 22

Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

Hancock condo

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$451

1 / 9

ROOM walking distance to Mass MoCa

North Adams apartment

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$101

1 / 14

Nasturtium Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$151

1 / 4

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$201

1 / 8

Perfect for skiers in the Berkshires

Lee townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$118

1 / 14

|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 1 hour 37 minutes

Price per night from

$451

1 / 31

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$286

1 / 20
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