Guesthouse vacation rentals in The Berkshires
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in The Berkshires
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Guesthouse in Tivoli
4.94 out of 5 average rating, 213 reviewsLight-filled guest cottage
Guesthouse in Woodstock
4.86 out of 5 average rating, 836 reviewsRocket Room - Rock Stars Only
Guesthouse in Belchertown
4.94 out of 5 average rating, 138 reviewsAmherst Area Studio Apartment
Guesthouse in Brattleboro
5.0 out of 5 average rating, 200 reviewsLight Filled Loft in the Vermont Countryside
Guesthouse in Northampton
4.93 out of 5 average rating, 241 reviewsLarge Studio – Walk to Town
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Guesthouse in Putney
4.95 out of 5 average rating, 323 reviewsA Vermont Carriage House
Guest house rentals with a patio
Guesthouse in Mahopac
4.93 out of 5 average rating, 119 reviewsSunny Lakeview Guesthouse
Guesthouse in Gardiner
4.99 out of 5 average rating, 140 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Guesthouse in Brewster
4.94 out of 5 average rating, 102 reviewsSherwood Barn - close to ski mountain
Guesthouse in Montgomery
4.94 out of 5 average rating, 125 reviewsLuxury mins from angry orchard and city winery
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 127 reviewsWake up at the Track on Historic Union Ave!!!
Guesthouse in Sharon
5.0 out of 5 average rating, 66 reviewsCottage with a Waterfall View
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Guesthouse in New Milford
5.0 out of 5 average rating, 44 reviewsLuxury in the Litchfield Hills
Guest house rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 212 reviewsNetherwood - North Adams Guest House with Views
Guesthouse in Glastonbury
4.96 out of 5 average rating, 134 reviewsUnique luxurious private building in historic area
Guesthouse in Fort Plain
4.98 out of 5 average rating, 448 reviewsStarhaven: Baseball HoF, Mineral Mining & More
Guesthouse in Brewster
5.0 out of 5 average rating, 291 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Guesthouse in Marlboro
4.99 out of 5 average rating, 142 reviewsRefined, serene and like no other, Marlboro, VT.
Guesthouse in Beacon
4.94 out of 5 average rating, 369 reviewsCozy Mountainside Suite - Minutes from Beacon
Guesthouse in Stanfordville
4.92 out of 5 average rating, 165 reviewsEco Cottage in the Woods
Guesthouse in Woodstock
5.0 out of 5 average rating, 303 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Long Island
- Guesthouse rentals Long Island
- House rentals New York
- Guesthouse rentals New York
- Pet-friendly rentals The Berkshires
- Cabin rentals The Berkshires
- Kid-friendly rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Rentals with a hot tub The Berkshires
- Smoking-friendly rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Farmstay rentals The Berkshires
- Vacation home rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Rentals with a kayak The Berkshires
- Lakehouse rentals The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Rentals with a washer and dryer The Berkshires
- Rentals with a home theater The Berkshires
- Rentals with pools The Berkshires
- Rentals with outdoor seating The Berkshires
- Waterfront rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Cottage rentals The Berkshires
- Rentals with beach access The Berkshires
- Rentals with a sauna The Berkshires
- Monthly Rentals The Berkshires
- Rentals with breakfast The Berkshires
- Aparthotel rentals The Berkshires
- House rentals The Berkshires
- Rentals with a patio The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Wheelchair accessible rentals The Berkshires
- Rentals with a fire pit The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Townhouse rentals The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom