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Featured Western Massachusetts Winery Hotels
The Old Inn On The Green
134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
Stay at this 4-star inn in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library ...
Shaker Mill Inn
2 Oak Street, West Stockbridge, MA
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd, West Stockbridge, MA
Fully refundableReserve now, pay when you stay
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Chesapeake Inn of Lenox
210 West Street, P.O. Box 1920, Lenox, MA
Stay at this 3-star golf B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
Monument Mountain Motel
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Book a stay at this spa hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Lantern House Motel
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Garden Gables Inn
135 Main St, Lenox, MA
Stay at this 4-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Bookstore and Lenox Library are located ...
The Cornell Inn, Lenox
203 Main St, Lenox, MA
Stay at this 3-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. ...
Whistler's Inn Bed & Breakfast
5 Greenwood Street, Lenox, MA
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Bookstore and Lenox Library are located ...
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.
Hotels by Star Rating
More Hotel Options in Western Massachusetts
- Hotels with Free Parking in Western Massachusetts
- Family Hotels in Western Massachusetts
- Historic Hotels in Western Massachusetts
- Hotels with a Pool in Western Massachusetts
- Luxury Hotels in Western Massachusetts
- Pet-friendly Hotels in Western Massachusetts
- Hotel Wedding Venues in Western Massachusetts
- Resorts & Hotels with Spas in Western Massachusetts
- Hotels with Hot Tubs in Western Massachusetts
- Romantic Hotels in Western Massachusetts
Western Massachusetts Neighborhoods
- Forest Park Hotels (25.27 mi)
- South End Hotels (23.84 mi)
- Six Corners Hotels (23.81 mi)
- Liberty Heights Hotels (21.89 mi)
- Boston Road Hotels (24.27 mi)
- East Forest Park Hotels (25.29 mi)
- Pelham Town Hall Historic District Hotels (22.85 mi)
- McKnight Hotels (22.96 mi)
- Old Hill Hotels (23.72 mi)
- East Village Historic District Hotels (17.83 mi)
Top Points of Interests in Western Massachusetts
- Hotels near MGM Springfield
- Hotels near University of Massachusetts Amherst
- Hotels near Six Flags New England
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Ski Butternut
- Hotels near Tanglewood Music Center
- Hotels near Catamount Ski Area
- Hotels near MassMutual Center
- Hotels near Eastern States Exposition
- Hotels near Naismith Memorial Basketball Hall of Fame
- Hotels near Amherst College
- Hotels near National Shrine of the Divine Mercy
- Hotels near Big E
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Berkshire East Ski Resort
- Hotels near Williams College
- Hotels near Smith College
- Hotels near Mount Holyoke College
- Hotels near Bousquet Ski Area
- Hotels near Holyoke Mall
Cities near Western Massachusetts
- Hartford Hotels (43.02 mi)
- Upstate New York Hotels (149.44 mi)
- Springfield Hotels (23.21 mi)
- West Dover Hotels (39.02 mi)
- Sturbridge Hotels (43.72 mi)
- The Catskills Hotels (91.54 mi)
- Lenox Hotels (21.95 mi)
- Hudson Hotels (48.5 mi)
- The Berkshires Hotels (20.75 mi)
- Rhinebeck Hotels (62.31 mi)
- Northampton Hotels (11.43 mi)
- Great Barrington Hotels (28.65 mi)
- Brattleboro Hotels (36.31 mi)
- Windsor Hotels (37.58 mi)
- Stockbridge Hotels (24.48 mi)
- Pittsfield Hotels (20.97 mi)
- Williamstown Hotels (29.32 mi)
- Amherst Hotels (17.11 mi)
- Windsor Locks Hotels (32.84 mi)
- Hudson Valley Hotels (78.31 mi)
Car Rentals near Western Massachusetts
- Car rentals in Hartford
- Car rentals in Upstate New York
- Car rentals in Springfield
- Car rentals in West Dover
- Car rentals in Sturbridge
- Car rentals in The Catskills
- Car rentals in Lenox
- Car rentals in Hudson
- Car rentals in The Berkshires
- Car rentals in Rhinebeck
- Car rentals in Northampton
- Car rentals in Great Barrington
- Car rentals in Brattleboro
- Car rentals in Windsor
- Car rentals in Stockbridge
- Car rentals in Pittsfield
Top Winery Hotel Destinations
- Long Island Winery Hotels
- Niagara On The Lake Winery Hotels
- Charlottesville Winery Hotels
- Southern California Winery Hotels
- Upstate New York Winery Hotels
- Hudson Valley Winery Hotels
- Ensenada Winery Hotels
- Kansas City Winery Hotels
- Newport Winery Hotels
- San Luis Obispo Winery Hotels
- Dallas Winery Hotels
- San Diego Winery Hotels
- Lexington Winery Hotels
- Phoenix Winery Hotels
- Cleveland Winery Hotels
- Escondido Winery Hotels
- Chicago Winery Hotels
- Philadelphia Winery Hotels
- Nashville Winery Hotels
- Los Angeles Winery Hotels
Top Booked Hotels in Western Massachusetts
- MGM Springfield
- D. Hotel Suites & Spa
- Holiday Inn Express Springfield Downtown, an IHG Hotel
- Hotel Downstreet
- La Quinta Inn & Suites by Wyndham Springfield MA
- Tru by Hilton Chicopee Springfield
- The Yankee, Trademark Collection by Wyndham
- The Red Lion Inn
- Hampton Inn & Suites Springfield/Downtown
- Quality Inn