Book Guest Houses in Monterey, MA

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Guest Houses in Monterey

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Oct 25 - Oct 26

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.

Pet friendly

Parking included

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$147 total

Nov 10 - Nov 11

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.

Pet friendly

Parking included

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$189 nightly

$211 total

Oct 26 - Oct 27

Total with taxes and fees

This guesthouse includes a garden and barbecue grills.

Free WiFi

Air conditioning

The Dewey

7 Hubbard Street Lenox MA

Get rates

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Parking included

Free WiFi

9 Academy

9 Academy St Salisbury CT

$517 nightly

$594 total

Oct 25 - Oct 26

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.

Parking included

Free WiFi

Hudson valley and The Berkshires Cottage

Hillsdale NY

Get rates

A garden is available at this guesthouse.

Pet friendly

Free WiFi

Renovated Private Guest House by Evergreen Home

Great Barrington MA

Get rates

This guesthouse features a garden, laundry facilities, and barbecue grills.

Pet friendly

Free WiFi

Cliffwood Cottage by Evergreen Home

Lenox MA

Get rates

This guesthouse features laundry facilities.

Free WiFi

Air conditioning

Chestnut Lodge

75 Chestnut Street Lee MA

Get rates

A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.

Hot Tub

Parking included

Jacob's Tanglewood Ranch

560 Stockbridge Rd Lee MA

Get rates

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.

Pet friendly

Parking included

Vanderbilt Lakeside

161 Main St Philmont NY

Get rates

This guesthouse features free WiFi in public areas, wedding services, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a communal living room are also on offer.

Breakfast included

Parking included

Don't see what you're looking for?

See all available properties in Monterey

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.

Top hotels in Monterey

The Yankee Inn

461 Pittsfield Rd Lenox MA

$101 nightly

$112 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,002 reviews)

Monterey Guest Houses essential information

Accommodation	11 Guest Houses
Lowest Price	$85
Highest Price	$594
Popular accommodation	The Central Downtown Inn & Suites, Hideaway Inn Lenox, Berkshire Village Carriage House - Super Private!!, The Dewey, 9 Academy , Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Chestnut Lodge, Jacob's Tanglewood Ranch, Vanderbilt Lakeside