Hillsdale hotels from RM279
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Hillsdale
Pet friendly
Apartยญment
Family friendly
Cottage
Waterpark
Condo
Check prices for these dates
Tonight
1 Sept - 2 SeptTomorrow
2 Sept - 3 SeptThis weekend
4 Sept - 6 SeptNext weekend
11 Sept - 13 SeptOur top choices for Hillsdale hotels
1. The Brooks Motel
The Brooks MotelHillsdale
Nelson
RM587
RM658 total
includes taxes & fees
2 Sept - 3 Sept
2. Little Cat Lodge
Little Cat LodgeCopake Falls
Kees
RM721
RM808 total
includes taxes & fees
2 Sept - 3 Sept
3. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
RM532
RM594 total
includes taxes & fees
15 Sept - 16 Sept
4. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
Lisa
RM647
RM723 total
includes taxes & fees
7 Sept - 8 Sept
5. Quality Inn Great Barrington
Quality Inn Great BarringtonGreat Barrington
Sisile
RM373
RM417 total
includes taxes & fees
22 Sept - 23 Sept
6. Prospect Berkshires
Prospect BerkshiresEgremont
Kellee
RM1,322
RM1,612 total
includes taxes & fees
24 Sept - 25 Sept
7. the Alander
the AlanderCopake
Phil
RM582
RM652 total
includes taxes & fees
17 Sept - 18 Sept
8. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
Charlie
RM344
RM384 total
includes taxes & fees
2 Sept - 3 Sept
9. Wilder House Berkshires
Wilder House BerkshiresSheffield
Jennifer
RM807
RM902 total
includes taxes & fees
10 Sept - 11 Sept
10. Granville House
Granville HouseHousatonic
Nicole
RM1,107
RM1,236 total
includes taxes & fees
17 Sept - 18 Sept
11. The Little Lion
The Little LionGreat Barrington
Anne
RM453
RM506 total
includes taxes & fees
13 Sept - 14 Sept
12. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
Elspeth
RM342
RM382 total
includes taxes & fees
13 Sept - 14 Sept
13. East Rock Inn
East Rock InnGreat Barrington
ERIK
RM591
RM660 total
includes taxes & fees
22 Sept - 23 Sept
14. Shaker Mill Inn
Shaker Mill InnWest Stockbridge
Mervin
RM656
RM720 total
includes taxes & fees
8 Sept - 9 Sept
15. Changing Times Boutique Country Lodging
Changing Times Boutique Country LodgingCraryville
Thomas
RM805
RM902 total
includes taxes & fees
2 Sept - 3 Sept
16. The Red Lion Inn
The Red Lion InnStockbridge
Patricia
RM666
RM944 total
includes taxes & fees
3 Sept - 4 Sept
17. Micosta Leisure Inn
Micosta Leisure InnHudson
Andrea
RM515
RM577 total
includes taxes & fees
7 Sept - 8 Sept
18. Charming 6 Bdrm Countryside Stay
Charming 6 Bdrm Countryside StayGreat Barrington
RM1,457
RM3,641 total
includes taxes & fees
8 Sept - 9 Sept
19. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
RM441
RM493 total
includes taxes & fees
24 Sept - 25 Sept
20. Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West StockbridgeWest Stockbridge
Peter
RM304
RM334 total
includes taxes & fees
8 Sept - 9 Sept
Stay near popular Hillsdale attractions
Catamount Aerial Adventure Park
6.4/10 (5 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
Copake Lake
This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.
Hillsdale Town Hall
This historic former library now serves as Hillsdale's administrative centre with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.
Mosquito Island
Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
Community Library
The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.
Roe Jan Brewing Co.
After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.
Learn more about Hillsdale
Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.
See all hotels in Hillsdale
Top Hillsdale Hotel Reviews
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"outstanding"
Berkshire Mountain Lodge
10/10 Excellent
"Enjoyed my stay! Spacious rooms, clean, quiet, surrounded by nature, free custom coffee โ๏ธ in lobby, free laundry facilities (bring your own detergent), no restaurant on-site. Pittsfield had lots of dining options nearby. I recommend the local nature trails at the Audubon Sanctuary, so beautiful ๐"
The Red Lion Inn
10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Howard Johnson by Wyndham Saugerties
8/10 Good
"Clean comfortable room and restaurant."
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
8/10 Good
"The room was very quiet"
Hotel On North
8/10 Good
"Nice room! Comfortable bed. Super friendly staff."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"It was clean and amenities were above average."
Pocketbook Hotel and Bath
8/10 Good
"Gorgeous stay - need to work out some kinks. Had to ask for a steamer 3 times to never get one. 3 times for extra pillows. The valet parking situation is a bit off. Hotel staff talking loudly with non guests how they wouldnโt spend the money to stay here. Our room had a window that was directly in the way of morning light with a window that had NO shade - brought this up and nothing was done nor apologized. The rooms are LOUD - yes the property is old and they make note but when you have old and steel tubs you need to add rugs in the room minimum. The aesthetic is beautiful and the design firm did great but if you want to charge these prices that Iโm sure will climb you need to fix these small details. The restaurant was the star out our trip absolutely incredible food and lovely staff. Overall a good stay but again - some changes need to be made as you know the crowd you are attracting."
More cheap stays in Hillsdale
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
RM250
RM279 total
7 Sept - 8 Sept
includes taxes & fees
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
RM318
RM355 total
3 Sept - 4 Sept
includes taxes & fees
7.6/10 Good! (907 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
RM348
RM389 total
28 Sept - 29 Sept
includes taxes & fees
Quality Inn Great Barrington
372 Main Street Great Barrington MA
RM373
RM417 total
22 Sept - 23 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
RM475
RM531 total
8 Sept - 9 Sept
includes taxes & fees
9.2/10 Wonderful! (181 reviews)
Pocketbook Hotel and Bath
549 Washington Street Hudson NY
RM813
RM1,100 total
9 Sept - 10 Sept
includes taxes & fees
8.4/10 Very good! (70 reviews)
