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Pet Friendly Holiday Rentals in Berkshires

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37 rentals in Berkshires.
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Lakefront Berkshires Ski/Summer House, Great Views
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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3 other travellers have booked this property
Unique People & Pet-Welcoming Country Haven
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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24 other travellers have booked this property
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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14 other travellers have booked this property
Cozy and clean in Gt Barrington- available for October
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Charming Farmhouse on Magical 4 Acre Estate
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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4 other travellers have booked this property
Romantic Berkshire Cottage on Storybook Estate
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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6 other travellers have booked this property
Berkshire Farmhouse Vacation
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps, Pet friendly
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18 other travellers have booked this property
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Escape to the Berkshires!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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6 other travellers have booked this property
Apartment walking distance to Mass MoCa!!
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps, Pet friendly
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9 other travellers have booked this property
House On Main Street
4 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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ROOM walking distance to Mass MoCa
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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4 other travellers have booked this property
3 BR apartment, walking distance to Mass MoCa
3 bedrooms
1 bathroom
Sleeps 15
Match: Sleeps, Pet friendly
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3 other travellers have booked this property
Enjoy horses and the largest recreational lake in Massachusetts
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Tranquil 3BR Stockbridge House w/Private Deck
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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3 other travellers have booked this property
Iris Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Horse Room
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Fox Hollow Laurel Lake Ranch
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps, Pet friendly
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3 other travellers have booked this property
Designer Loft Style Residence
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Cozy Modern Condo for the Berkshires
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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2 other travellers have booked this property
One of the Finest Homes and Best location in the Berkshires
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Serene Lakefront Cottage
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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1 other traveller has booked this property
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
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Pet-Friendly Berkshires Home w/Dock & Fire Pit!
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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The Bear Den
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Tentrr Signature - Berkshire Mountain Hideaway
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Tentrr Signature - Echo Hill
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps, Pet friendly
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Tentrr Signature - Hidden Hoosic Riverside Camp
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Tentrr Signature - Running Spring Farm
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Tentrr Signature - Round Mountain Camp
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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'The Mill River Cabin’ w/ Fireplace & River View!
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Pet friendly
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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Tentrr Signature - The Lodge's Campsite
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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