Compare The Berkshires Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in The Berkshires

$109 nightly

$122 total

Apr 5 - Apr 6

Total with taxes and fees

Guests of The Central Downtown Inn & Suites enjoy free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a terrace and laundry facilities.

Berkshire Village Carriage House - Super Private!!

$185 nightly

$207 total

Apr 4 - Apr 5

Total with taxes and fees

Guests staying at this guesthouse have access to barbecue grills and a garden.

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$168 total

Apr 5 - Apr 6

Total with taxes and fees

The Revival House features free WiFi in public areas and a communal living room. There's free parking if you drive.

At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.

Renovated Private Guest House by Evergreen Home

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.

Guests staying at Jacob's Tanglewood Ranch enjoy free WiFi in public areas, a terrace, and a picnic area. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a fireplace in the lobby.

At this guesthouse, guests have access to features like laundry facilities.

At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.

Don't see what you're looking for?

See all available properties in The Berkshires

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in The Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$126 nightly

$141 total

Apr 5 - Apr 6

Total with taxes and fees

8.8/10 Excellent! (2,322 reviews)

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

$131 nightly

$146 total

May 3 - May 4

Total with taxes and fees

8.8/10 Excellent! (1,000 reviews)

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$108 nightly

$120 total

May 3 - May 4

Total with taxes and fees

9/10 Wonderful! (894 reviews)

The Berkshires Guest Houses essential information

Accommodation	8 Guest Houses
Lowest Price	$120
Highest Price	$207
Popular accommodation	The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Revival House, The Dewey, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge