
Guest house holiday rentals in Berkshire County
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Berkshire County
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Berkshire County
Family-friendly guest house rentals

The East Street Cabin

Brookside Cottage

Dog Friendly Studio

Restored 1735 Granary I King Bed + Views & Pool

Modern studio with views of the treetops

The Coach House | Modern 2BR Loft + Views & Pool

Modern barn in the heart of the Berkshires

Sweet Victorian in Housatonic
Guest house rentals with a patio

The Nest at Birdland

Light-filled Carpenter's Cottage in Stockbridge

Berkshires Guest Barn

Cottage with exquisite views

The Recording Studio @ Moonbeams

1-bed unit 3/4 mi. from GB dwntwn.

Guest House at Stonover Estate

New-Modern! Guest House with Shared Pool
Guest house rentals with a washing machine and dryer

The Blue Jay Cottage

Bella Rena Guesthouse

2 bedroom Guest House

Cliffwood Cottage by Evergreen Home

House of HBB: (Downstairs) Historic Registry 1815

House of HBB: (Upstairs) with Mountain views

Zen 1738 Retreat: near Tanglewood, Jacob's Pillow

224 Lodge -Skiing/Entertainment
Destinations to explore
- Rentals with pools Berkshire County
- Aparthotel rentals Berkshire County
- Rentals with a patio Berkshire County
- Waterfront rentals Berkshire County
- House rentals Berkshire County
- Bed and breakfasts Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with a sauna Berkshire County
- Flat rentals Berkshire County
- Rentals with lake access Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Hotel rentals Berkshire County
- Cottage rentals Berkshire County
- Rentals with a firepit Berkshire County
- Rentals with a kayak Berkshire County
- Fitness-friendly rentals Berkshire County
- Private suite rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with an EV charger Berkshire County
- Farm stay rentals Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Beachfront rentals Berkshire County
- Rentals with beach access Berkshire County
- Chalet rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Guest house rentals Massachusetts
- Guest house rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bushnell Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Taconic State Park
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden
- Mount Snow Ski Resort