Pittsfield Guest Houses

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Guest Houses in Pittsfield

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA

$155 nightly

$173 total

Jun 7 - Jun 8

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

When you stay at Hideaway Inn Lenox in Lenox, you'll be near ski lifts, within a 5-minute drive of Shakespeare and Company and Tanglewood Music Center.

Pet friendly

Parking included

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$114 nightly

$127 total

Jun 7 - Jun 8

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.

Pet friendly

Parking included

The Revival House

17 Commercial St Adams MA

$166 nightly

$185 total

Jun 16 - Jun 17

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at The Revival House in Adams, you'll be a 5-minute walk from Adams Theater and 10 minutes by foot from Berkshire Scenic Railway Museum.

Breakfast included

Parking included

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$257 nightly

$287 total

Jun 29 - Jun 30

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.

Free WiFi

Air conditioning

Hudson valley and The Berkshires Cottage

Hillsdale NY

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.

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.

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.

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.

Free WiFi

Air conditioning

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.

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.

Hot Tub

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.

Pittsfield Guest Houses essential information

Accommodation	10 Guest Houses
Lowest Price	$127
Highest Price	$287
Popular accommodation	Hideaway Inn Lenox, The Central Downtown Inn & Suites, The Revival House, Berkshire Village Carriage House - Super Private!!, Hudson valley and The Berkshires Cottage, The Dewey, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside, Chestnut Lodge