Book Guest Houses in Monterey, MA

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Top Guest Houses in Monterey

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$85 nightly

$95 total

Dec 7 - Dec 8

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

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$189 nightly

$211 total

Dec 8 - Dec 9

Total with taxes and fees

This guesthouse includes a garden and barbecue grills.

Free WiFi

Air conditioning

9 Academy

9 Academy St Salisbury CT

$494 nightly

$568 total

Dec 8 - Dec 9

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

The Dewey

7 Hubbard Street Lenox MA

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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

Hudson valley and The Berkshires Cottage

Hillsdale NY

$305 nightly

$310 total

Dec 15 - Dec 16

Total with taxes and fees

This guesthouse includes a garden and laundry facilities.

Pet friendly

Free WiFi

Renovated Private Guest House by Evergreen Home

Great Barrington MA

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

Pet friendly

Free WiFi

Jacob's Tanglewood Ranch

560 Stockbridge Rd Lee MA

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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

Chestnut Lodge

75 Chestnut Street Lee MA

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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

Cliffwood Cottage by Evergreen Home

Lenox MA

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This guesthouse features laundry facilities.

Free WiFi

Air conditioning

Vanderbilt Lakeside

161 Main St Philmont NY

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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

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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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$108 nightly

$120 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

9/10 Wonderful! (773 reviews)

Monterey Guest Houses essential information

Accommodation	10 Guest Houses
Lowest Price	$95
Highest Price	$568
Popular accommodation	The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, 9 Academy , The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside