Photo by Photo courtesy of Berkshire Visitors Bureau
Search Guest Houses in The Berkshires
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for The Berkshires guest houses
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
Lynn
The price is €89
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!Lanesborough
9.8 out of 10, Exceptional, (271)
"What an ideal place to make home base for an extended weekend in the Berkshires with activities. Place is a gem in the woods but accessible to everything. "
liz k.
The price is €182
includes taxes & fees
28 Dec - 29 Dec
9.0 out of 10, Wonderful, (25)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
melissa
The price is €142
includes taxes & fees
29 Dec - 30 Dec
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
Tami
The price is €210
includes taxes & fees
3 Jan - 4 Jan 2026
9.2 out of 10, Wonderful, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
Allison
The price is €105
includes taxes & fees
5 Jan - 6 Jan 2026
In town, newly remodeled studio with private balcony
In town, newly remodeled studio with private balconyShelburne Falls
10.0 out of 10, Exceptional, (119)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
Marina G.
The price is €130
includes taxes & fees
8 Jan - 9 Jan 2026
Hudson valley and The Berkshires Cottage
Hudson valley and The Berkshires CottageHillsdale
10.0 out of 10, Exceptional, (17)
"Wonderful place - great location. Beautiful cottage and perfectly designed. Had everything we needed for a lone weekend."
Lauren P.
The price is €290
includes taxes & fees
5 Jan - 6 Jan 2026
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.
Top The Berkshires Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
Find out more about The Berkshires
The Berkshires Guest Houses information
Number of reviews | 1,078 |
|---|---|
Accommodation | 8 Guest Houses |
Lowest Price | €89 |
Highest Price | €481 |
Explore a world of travel with Expedia
- 4 Star Hotels in Chester
- 4 Star Hotels in Granville
- 4 Star Hotels in Western Massachusetts
- Agawam Hotels
- Alford Hotels
- Becket Hotels
- Cabin Rentals in Cheshire
- Apartments in Chesterfield
- Dalton Hotels
- Florence Hotels
- Hotels near Fun Time Lanes
- Apartments in Granville
- Cheap Hotels in Great Barrington
- Hotels with Spa in Great Barrington
- Great Barrington Hotels
- Hotels with Spa in Hancock
- Hancock Hotels
- Holyoke Hotels
- Holiday Homes in Indian Orchard
- Hotels near Jacob's Pillow
- Hotels near Kennedy Park
- Apartments in Lee
- Historic Hotels in Lee
- Lee Hotels
- Cheap Hotels in Lenox
- Lenox Hotels
- Apartments in Longmeadow
- Cabin Rentals in Mohawk Trail State Forest
- Motels in Monson
- Hotels near National Shrine of the Divine Mercy
- Cabin Rentals in October Mountain State Forest
- Otis Hotels
- Luxury Hotels in Pittsfield
- Hotels with Spa in Pittsfield
- Pittsfield Hotels
- Plainfield Hotels
- Richmond Hotels
- Russell Hotels
- Savoy Hotels
- Cabin Rentals in Sheffield
- Southfield Hotels
- Southwick Hotels
- Apartments in Springfield
- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Cabin Rentals in The Berkshires
- Cottages in The Berkshires
- Boutique Hotels in The Berkshires
- Cheap Hotels in The Berkshires
- Hotels with Spa in The Berkshires
- West Springfield Hotels
- West Stockbridge Hotels
- Cabin Rentals in Western Massachusetts
- Castles in Western Massachusetts
- Luxury Hotels in Western Massachusetts
- Westfield Hotels
- Windsor Hotels
- Visit Agawam
- Becket Land Trust Historic Quarry
- Visit Sherwood Forest
- Visit Becket
- Berkshire Botanical Garden
- Charles H. Baldwin & Sons
- Chesterfield Holidays
- Chesterwood
- Visit Great Barrington
- Visit Hancock
- Lee Holidays
- Visit Lee
- Romantic Holiday Packages The Berkshires
- Mclennan Reservation
- Visit Middlefield
- National Shrine of the Divine Mercy
- Naumkeag Museum
- Otis Holidays
- Visit Pittsfield
- Visit South Lee
- Visit Southampton
- Tanglewood Music Center
- Visit Western Massachusetts