Hillsdale
Travel Guide
Visit Hillsdale
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $180 per night from Jul 6 to Jul 7
CA $180
CA $202 total
Jul 6 - Jul 7
includes taxes & fees
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 ...
9.2/10 Wonderful! (1,000 reviews)
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical ..."
Reviewed on Jul 2, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is CA $190 per night from Aug 2 to Aug 3
CA $190
CA $244 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,010 reviews)
"The hotel was nice, full kitchen and quiet large for our family of four. We had a one bedroom suite, tucked into a corner of the hotel. Location was quiet, on the main floor. Pool and hot tub were nice. The sofa bed was not comfortable, at all. It would be worth the hotel replacing the sofa bed, ..."
Reviewed on Jul 2, 2026
The Red Lion Inn
30 Main Street Stockbridge MA
The price is CA $263 per night from Jul 20 to Jul 21
CA $263
CA $357 total
Jul 20 - Jul 21
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"Staff was great. Cool place - so historic"
Reviewed on Jun 30, 2026
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.
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Austerlitz NY
Stay at this vacation home in Hillsdale. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Art et Industrie and Hoffman's Pottery are located ...
10/10 Exceptional! (19 reviews)
"The location is ideal for exploring the Berkshires and cute nearby communities. The interior of the home is updated and comfortable (I’m buying the duvet set for myself!) The yard is not fully fenced in as we were hoping to let our dogs off leash, but we found a great dog park nearby."
Reviewed on Oct 14, 2025
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
9.6/10 Exceptional! (253 reviews)
"I brought my wife to the Poscard Cabin because a friend of owers told me about it. I have to tell you my wife had a blast we came here to celebrate her 66th Birthay and ower 20 years anniversary and it was the best choice I made. I will recommend to everyone I know."
Reviewed on Jul 1, 2026
Micosta Leisure Inn
3007 County Rd 20 Hudson NY
Book a stay at this business-friendly aparthotel in Hudson. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions FASNY Museum of Firefighting ...
9.2/10 Wonderful! (155 reviews)
"Was fine for the price. Wished the room was ready at 2pm check in, otherwise no issues."
Reviewed on Jun 29, 2026
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.
Stay near popular Hillsdale attractions
Explore a world of travel with Expedia
- Lodges in Athens
- Claverack Hotels
- Old Chatham Hotels
- Coxsackie Hotels
- Rv Parks in Oakdale
- Farmstay in Pine Plains
- Hillsdale Hotels
- Stottville Hotels
- Pine Plains Hotels
- Hudson Hotels
- Pet-Friendly Hotels in Athens
- Nassau Hotels
- Spacious Warren St. apt in the heart of Hudson
- Pet-Friendly Hotels in Canaan
- Cabin Rentals in Millerton
- Philmont Hotels
- Beach Hotel Hotels in Hudson
- Berkshire Travel Lodge
- Inns in Pine Plains
- Athens Hotels
- Niverville Hotels
- Four Seasons Motel
- Albany Hotels
- Motels in Niverville
- B&B in Athens
- Jefferson Heights Hotels
- Chatham Hotels
- B&B in Hudson
- Red Carpet Inn Hotels in Coxsackie
- Apartment In Historic 1785 Thomas Jenkins House
- Canaan Hotels
- Red Ranch Motel
- Hudson River Retreat
- Holiday Inn Express Hotel & Suites West Coxsackie by IHG
- Catskill Hotels
- Cabin Rentals in Catskill
- B&B in Chatham
- Hotels with Bar in Hudson
- Kinderhook Hotels
- Cheap Hotels in Hudson
- Cabin Rentals in Chatham
- 4 Star Hotels in Hudson
- Flights from Millerton
- Flights to Elizaville
- Flights from Augusta (AGS) to Hudson (HCC)
- Flights from Cancun (CUN) to Hudson (HCC)
- Flights to Hudson
- Flights from Ancramdale
- Flights from Bangor (BGR) to Hudson (HCC)
- Flights to Catskill
- Flights from Milwaukee (MKE) to Hudson (HCC)
- Flights from Germantown
- Flights from Hillsdale
- Flights from Toronto (YYZ) to Albany (ALB)
- Visit Acra
- Visit Malden Bridge
- Mohonk Preserve Visitor Center
- Visit Elka Park
- Visit Windham
- Visit Stanfordville
- Visit Clifton Park
- Visit Hudson Valley
- Visit Woodlawn
- Visit Newburgh
- Visit Albany
- Visit Poughkeepsie
- Visit Capitol - Saratoga Region
- Visit Downtown Albany
- Max and Lillian Katzman Theater
- Visit Melrose
- Visit Town of Stanford
- Visit Helderberg
- Visit Castle Point
- Shaker Museum and Library
- Visit Millbrook
- Visit Hampton Manor
- Visit Warehouse District
- Visit Waterford
- Catskill Vacations
- Visit Green Island
- Visit Buckingham Lake - Crestwood
- Visit Rhinebeck
- Visit East Durham
- Visit Rosendale
- Visit Crestwood
- Visit Hudson
- Visit Krumville
- Visit Red Oaks Mill
- Olana State Historic Site
