Hillsdale Guest Houses

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Guest Houses in Hillsdale

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$85 nightly

$95 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$189 nightly

$211 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Lanesborough, this guesthouse is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

9 Academy

9 Academy St Salisbury CT

$494 nightly

$568 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Salisbury, 9 Academy is a 1-minute drive from Harney and Sons Tea Tasting Room and 5 minutes from Mount Riga State Park.

The Dewey

7 Hubbard Street Lenox MA

With a stay at The Dewey in Lenox, you'll be in the suburbs, within a 5-minute drive of Tanglewood Music Center and The Bookstore.

Hits | Catskills Views | Pet Friendly | Studio

Saugerties NY

With a stay at this guesthouse in Saugerties, you'll be within a 15-minute walk of Bristol Beach State Park and HITS-on-the-Hudson.

Hudson valley and The Berkshires Cottage

Hillsdale NY

$304 nightly

$309 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this guesthouse in Hillsdale, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.

LEEDS A GREAT ESCAPE

Leeds NY

Located in Catskill, this guesthouse is in a rural location, a 5-minute drive from Catskill Golf Club and 5 minutes from Thomas Cole National Historic Site.

Renovated Private Guest House by Evergreen Home

Great Barrington MA

Located in Great Barrington, this guesthouse is in a rural location, within a 10-minute drive of Monument Mountain and Housatonic River.

Jacob's Tanglewood Ranch

560 Stockbridge Rd Lee MA

With a stay at Jacob's Tanglewood Ranch in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

1805 House Bed and Breakfast

775 Snydertown Road Craryville NY

Located in Craryville, 1805 House Bed and Breakfast is in a rural location, within a 15-minute drive of Claverack Library and Stoddard Corner.

Chestnut Lodge

75 Chestnut Street Lee MA

With a stay at Chestnut Lodge in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Cliffwood Cottage by Evergreen Home

Lenox MA

With a stay at this guesthouse, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and The Bookstore.

Don't see what you're looking for?

See all available properties in Hillsdale

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.