Search Guest Houses in The Berkshires from CA $158
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select The Berkshires Guest Houses

The Dewey
The Dewey
8.8 out of 10, Excellent, (321)
The price is CA $240
CA $268 total
includes taxes & fees
Sep 10 - Sep 11

The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
8.8 out of 10, Excellent, (301)
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2

The Revival House
The Revival House
9.4 out of 10, Exceptional, (10)
The price is CA $248
CA $277 total
includes taxes & fees
Aug 17 - Aug 18

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (254)

Renovated Private Guest House by Evergreen Home
Renovated Private Guest House by Evergreen Home
10.0 out of 10, Exceptional, (9)

Jacob's Tanglewood Ranch
Jacob's Tanglewood Ranch

Cliffwood Cottage by Evergreen Home
Cliffwood Cottage by Evergreen Home

Chestnut Lodge
Chestnut Lodge
2.0 out of 10, (2)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
Find out more about The Berkshires
Find out more about The Berkshires
The Berkshires Guest Houses information
Number of reviews | 751 |
---|---|
Accommodation | 9 Guest Houses |
Lowest Price | CA $158 |
Highest Price | CA $248 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
- Guest Houses in Williamstown
- Guest Houses in Lee
- Guest Houses in Hancock
- Guest Houses in Adams
- Guest Houses in Lanesborough
- Guest Houses in Sheffield
- Guest Houses in Stockbridge
- Guest Houses in Becket
- Guest Houses in Otis
- Guest Houses in Lenox
- Guest Houses in Pittsfield
- Guest Houses in North Adams
- Guest Houses in West Stockbridge
- Guest Houses in South Lee
- Guest Houses in Monterey
- Guest Houses in Great Barrington
Top Guest Houses in Other Destinations
More Accommodation Types in The Berkshires
- Vacation Homes in The Berkshires
- Apartments in The Berkshires
- Cottages in The Berkshires
- Condo Rentals in The Berkshires
- Resorts in The Berkshires
- Cabin Rentals in The Berkshires
- Motels in The Berkshires
- B&B in The Berkshires
- Farmstay in The Berkshires
- Inns in The Berkshires
- Aparthotels in The Berkshires
- Chalets in The Berkshires
- Condo Resorts in The Berkshires
- Lodges in The Berkshires
- RV Parks in The Berkshires
- Castles in The Berkshires
- Country Houses in The Berkshires
- Villas in The Berkshires
- Hotels
All Accommodation Types
Be inspired: Top Guest Houses destinations in 2025
- Niagara Falls Guest Houses
- Toronto Guest Houses
- Montreal Guest Houses
- Vancouver Guest Houses
- Ottawa Guest Houses
- Calgary Guest Houses
- Quebec Guest Houses
- Edmonton Guest Houses
- Halifax Guest Houses
- Victoria Guest Houses
- Kelowna Guest Houses
- Laurentians Guest Houses
- Winnipeg Guest Houses
- Kingston Guest Houses
- Mont-Tremblant Guest Houses
- Jasper Guest Houses
- Halifax Guest Houses
- Saint Ferreol les Neiges Guest Houses
- Tofino Guest Houses
- Saskatoon Guest Houses
More ways to book
Expedia's Latest Trends
Hotels
Vacation Rentals