Search for Cheap Deals onHotels in Hillsdale
Choose from 1819 Hillsdale Hotel Deals
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (636 reviews)
Beauty Berkshire stay
"This was one of my favorite hotels I have ever stayed in. The room and lounge/restaurant are beautiful. Rooms are super quiet, and the bed was incredibly comfortable. I am sure to return."
Reviewed on Jul 17, 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
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 ...
8.4/10 Very Good! (1,013 reviews)
"Friendliness and cleanliness"
Reviewed on Jul 15, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (676 reviews)
"Terrific place. Spacious, clean, comfortable."
Reviewed on Jul 18, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (821 reviews)
Comfy beds, chair, good closet, very clean
"Overnight stay while on a family visit. Comfortable room, good beds, great AC. Quiet as well."
Reviewed on Jul 13, 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (741 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."
Reviewed on Jul 1, 2025
Howard Johnson by Wyndham Saugerties
2764 Route 32, Saugerties, NY
Book a stay at this business-friendly hotel in Saugerties. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff and the clean rooms ...
7.4/10 Good! (1,001 reviews)
Clean quiet stay at convenient location
"Clean quiet stay at convenient location. Thr property is dated but well maintained. Bathroom mirror lighting was better than some way more newer hotels ive stayed ay."
Reviewed on Jul 15, 2025
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
12740 State Route 9 W, West Coxsackie, NY
Book a stay at this business-friendly hotel in West Coxsackie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (905 reviews)
"Did not like truck noise on highway."
Reviewed on Jul 9, 2025
The Red Lion Inn
30 Main Street, Stockbridge, MA
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,001 reviews)
"We could use the pool and other amenities available prior to our room being available. It was great to sit outside have dinner whilst listening to live music."
Reviewed on Jul 17, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,003 reviews)
"Loved the Yankee Inn!"
Reviewed on Jul 14, 2025
The Constance by the Lenox Collection
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (439 reviews)
Replace the shower head.
"Too much water wasted when taking a shower. Replace the shower head. The front desk guy was the nicest. Very attentive and service oriented."
Reviewed on Jul 15, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (513 reviews)
"Great area, very reasonable."
Reviewed on Jul 11, 2025
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd, Lenox, MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
"Ez drive to Lenox & Tanglewood....plenty of parking. Grabbed a room last minute & front desk was great about being sure it was ready. Husband happy to have a cookie at check-in! Always love having a coffee maker in room & nice little buffet breakfast included."
Reviewed on Jul 4, 2025
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 Booked Hotels in Hillsdale
- Best Western Plus Berkshire Hills Inn & Suites
- FairBridge Inn Express
- Howard Johnson by Wyndham Saugerties
- Holiday Inn Express Hotel & Suites West Coxsackie by IHG
- The Red Lion Inn
- The Yankee, Trademark Collection by Wyndham
- Berkshire Mountain Lodge
- Hampton Inn & Suites Berkshires-Lenox
- Quality Inn
- Howard Johnson by Wyndham Lenox
- Courtyard by Marriott Lenox Berkshires
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Hotels near Catamount Aerial Adventure Park
- Hotels near Tanglewood Music Center
- Hotels near Bard College
- Hotels near Jiminy Peak Mountain Resort
- Hotels near National Shrine of the Divine Mercy
- Hotels near Lime Rock Park
- Hotels near HITS-on-the-Hudson
- Hotels near Hudson River
- Hotels near Olana State Historic Site
- Hotels near Catamount Ski Area
- Hotels near Norman Rockwell Museum
- Hotels near Ski Butternut
- Hotels near Jacob's Pillow
- Hotels near The Mount
- Hotels near Lee Premium Outlets
- Hotels near Saugerties Village Beach
- Hotels near Saugerties Lighthouse
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