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Pet-friendly vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Treehouse · Lee
Gingerbread House Tower in the Berkshire Hills
Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.
$284 per night
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Entire chalet · Otis
Octagonal Glass Treehouse in Berkshires
This octagonal Massachusetts glass architectural gem welcomes guests with its uniquely-designed yet informal interior. You can cozy up around the wood-burning fireplace, while gazing out of the floor to ceiling windows onto the 7 private surrounding acres, or sit around the firepit and gaze at the stars. Use at as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving the property. Up to you!
$350 per night
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Tiny home · Lee
Enchanted Tiny Tower nestled in the Berkshires
Whimsical and romantic tower on the Santarella Estate in the heart of the Berkshires. Live out your own fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.
$266 per night

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Pet-friendly cabins in Berkshire County

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Entire cabin · North Adams
The Wampanoag Cabin @ The Wigwam Western Summit
$201 per night
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Entire cabin · Canaan
Newly Renovated Cabin in the Country
$325 per night
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Entire cabin · Mill River
Evolve | The Mill River Cabin’ - Fireplace & Views
$202 per night
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Entire cabin · Monterey
Secluded cabin with babbling brook
$229 per night
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Entire cabin · Sheffield
Large Cabin in Berkshires near GB & superb hiking
$241 per night
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Entire cabin · Sandisfield
Iconic Cabin in the Berkshires
$790 per night
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Entire cabin · Washington
Berkshires Log Cabin, Peace and Tranquility Awaits
$208 per night
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Entire cabin · North Adams
The Pocumtuck Cabin @ The Wigwam Western Summit
$192 per night
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Entire cabin · Becket
Waldtreff - quiet grand cabin
$250 per night
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Entire cabin · North Adams
The Mohawk Cabin @ Wigwam Western Summit
$198 per night
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Entire cabin · Lanesborough
Cozy stream-side cabin
$206 per night
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Entire cabin · East Nassau
Into the Woods- Berkshire Cabin Retreat!
$250 per night