Vacation Rentals & House Rentals in Stockbridge

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Fireplace
Wireless Internet
Air conditioning
Swimming pool

Private pool
Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Fax machine
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Pool or snooker table
Shared indoor pool
Trampoline
Video player
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Boat available
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
Secure parking

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Skiing – property near ski resort
Walking trips
Tennis in town
Nightlife

Water sports
Horse riding
Fishing
Golf within 30mins drive
Mountain Views
Waterfront

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21 Houses

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One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms
3 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$799

Great rentals within 20 miles that match your search

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$152

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 45 minutes

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Price per night from

$229

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms
2 bathrooms

sleeps 4

Match: Fireplace

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Price per night from

$206

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$719

Christmas in The Berkshires

Hancock condo

1 bedroom
2 bathrooms

sleeps 4

Match: Fireplace

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Price per night from

$257

The Barn at Copake Lake

Craryville barn

3 bedrooms
3 bathrooms

sleeps 14

Match: Fireplace

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Price per night from

$684

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms
5 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$571

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms
3 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$1,026

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

1 bedroom
1 bathroom

sleeps 6

Match: Fireplace

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Price per night from

$259

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

4 bedrooms
3 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$280

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

3 bedrooms
3 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$565

Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!

Old Chatham villa

9 bedrooms
5 bathrooms

sleeps 16

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Price per night from

$1,255

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms
2 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$250

Escape to Avalon Cottage in the Hudson Valley

Craryville house

3 bedrooms
2 bathrooms

sleeps 4

Match: Fireplace

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Price per night from

$343

Modern Copake Falls Getaway

Copake Falls apartment

1 bedroom
1 bathroom

sleeps 4

Match: Fireplace

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Price per night from

$102

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

6 bedrooms
5 bathrooms

sleeps 15

Match: Fireplace

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Price per night from

$792

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

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Price per night from

$487

Private Berkshire Escape Monthly Pricing Available

Lee house

4 bedrooms
2 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$659

Private Berkshire County Retreat

Sheffield house

3 bedrooms
3 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$686

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

3 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$572

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Stockbridge Rentals

Per night

21 Houses

One of the Finest Homes and Best location in the Berkshires

Modern Cozy Wooded Retreat

Beautifully decorated & immaculate log chalet

Charming 2+2 Lakeside Cottage on Best Lake in CT

The Meadow House 4 bdrm 4 bath house

Christmas in The Berkshires

The Barn at Copake Lake

Spacious Lakeside Berkshire Home

Chalet near 4 ski resorts with hot tub

UMIQUE Country Condo, 1BR 1 BA - NEW

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Mountainside Getaway @ Jiminy Peak In the Berkshires

Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!

Lakefront Berkshires Ski/Summer House, Great Views

Escape to Avalon Cottage in the Hudson Valley

Modern Copake Falls Getaway

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Hillhouse Log Cabin

Private Berkshire Escape Monthly Pricing Available

Private Berkshire County Retreat

Private Home Overlooking Stevens Lake (31 Night Min)

Viewing 21 of 21
rentals in Stockbridge

Also consider

Stockbridge Rentals

Per night

21 Houses

Viewing 21 of 21rentals in Stockbridge

Also consider

Viewing 21 of 21
rentals in Stockbridge