Monterey Guest Houses

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Guest Houses in Monterey

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

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

Pet friendly

Parking included

9 Academy

9 Academy St, Salisbury, CT

$568

includes taxes & fees

$494 per night

Nov 24 - Nov 25

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.

Parking included

Free WiFi

Hudson valley and The Berkshires Cottage

$295

includes taxes & fees

$295 per night

Nov 25 - Nov 26

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

Kitchen

Pet friendly

Sweet Dreams Retreat

When you stay at this guesthouse in Sandisfield, you'll be in the mountains and 7 minutes by car from Cookson State Forest.

Pool

Hot Tub

Renovated Private Guest House by Evergreen Home

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

Jacob's Tanglewood Ranch

560 Stockbridge Rd, Lee, MA

With a stay at Jacob's Tanglewood Ranch in Lee, you'll be within a 5-minute drive of Greenock Country Club and Berkshire Theatre Festival.

Pet friendly

Parking included

Chestnut Lodge

75 Chestnut Street, Lee, MA

With a stay at Chestnut Lodge in Lee, you'll be within a 5-minute drive of October Mountain State Forest and Housatonic River.

Vanderbilt Lakeside

161 Main St, Philmont, NY

Located in Philmont, Vanderbilt Lakeside is on a lake, within a 15-minute drive of High Falls Trail and Claverack Library.

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.