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Go beyond your typical stay in Hillsdale
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Family friendly
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Check prices for these dates
Tonight
22 Aug - 23 AugTomorrow
23 Aug - 24 AugNext weekend
28 Aug - 30 AugIn two weeks
4 Sept - 6 SeptOur top choices for Hillsdale hotels




1. The Brooks Motel
The Brooks MotelHillsdale
Nelson
NZ$246
includes taxes & fees
26 Aug - 27 Aug




2. Little Cat Lodge
Little Cat LodgeCopake Falls
Kees
NZ$352
includes taxes & fees
24 Aug - 25 Aug




3. Quality Inn Great Barrington
Quality Inn Great BarringtonGreat Barrington
Sisile
NZ$173
includes taxes & fees
13 Sept - 14 Sept




4. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
NZ$215
includes taxes & fees
20 Sept - 21 Sept




6. Prospect Berkshires
Prospect BerkshiresEgremont
Kellee
NZ$670
includes taxes & fees
17 Sept - 18 Sept




7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
Lisa
NZ$364
includes taxes & fees
26 Aug - 27 Aug




8. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
John
NZ$160
includes taxes & fees
1 Sept - 2 Sept




9. East Rock Inn
East Rock InnGreat Barrington
ERIK
NZ$235
includes taxes & fees
13 Sept - 14 Sept




10. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
Elspeth
NZ$148
includes taxes & fees
1 Sept - 2 Sept




11. Shaker Mill Inn
Shaker Mill InnWest Stockbridge
Mervin
NZ$296
includes taxes & fees
26 Aug - 27 Aug




12. Wilder House Berkshires
Wilder House BerkshiresSheffield
Jennifer
NZ$367
includes taxes & fees
1 Sept - 2 Sept




13. The Little Lion
The Little LionGreat Barrington
Anne
NZ$210
includes taxes & fees
1 Sept - 2 Sept




14. Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West StockbridgeWest Stockbridge
Peter
NZ$127
includes taxes & fees
24 Aug - 25 Aug




15. Granville House
Granville HouseHousatonic
Nicole
NZ$514
includes taxes & fees
26 Aug - 27 Aug




16. Changing Times Boutique Country Lodging
Changing Times Boutique Country LodgingCraryville
Thomas
NZ$375
includes taxes & fees
31 Aug - 1 Sept




17. Micosta Leisure Inn
Micosta Leisure InnHudson
Andrea
NZ$242
includes taxes & fees
27 Aug - 28 Aug




18. The Red Lion Inn
The Red Lion InnStockbridge
Patricia
NZ$375
includes taxes & fees
23 Sept - 24 Sept




19. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
NZ$205
includes taxes & fees
14 Sept - 15 Sept




20. Berkshire Travel Lodge
Berkshire Travel LodgeAusterlitz
Kris
NZ$126
includes taxes & fees
25 Aug - 26 Aug
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
Recent Reviews in Hillsdale
St. Charles Hotel
8/10 Good
"A no-frills hotel, but super pet-friendly and with the friendliest , most helpful staff. Very close to Warren St,ots of shops and restaurants around!"
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Lovely setting. Comfortable and well equipped townhouse. We are not much for the pool or mini golf type “activities” but we like the location near biking, hiking, theater and dance venues. And the ability to have meals in instead of using restaurants every meal. Looks like a great place for family vacations."
Berkshires Untold
8/10 Good
"We loved our stay and would return! The bar/lounge area is lovely and inviting. Super location to get to Lenox and Stockbridge. The rooms are motel style which isn't ideal and there are stairs/no elevator. Next time I would request an "even" room so as to not face the highway. Plentiful and easy parking."
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Howard Johnson by Wyndham Saugerties
10/10 Excellent
"Clean."
The Whitlock
8/10 Good
"The Whitlock is a lovely old inn, located right in the heart of Lenox and walkable to everything in town. The staff is also lovely. Our room was spacious and well layed out. [but for an ADA compliant walk in shower, you need more than grab bars - a rubber matt in the shower is a necessity!!] However, for a hotel that calls itself hi-end, it fell far short of that mark. First and foremost, the email communications with both Hotels.com and the The Whitlock were like a Marx Brothers skit: We were first told the check in would be at the Constance down the street, not at the Whitlock. When I asked the off-shore "team" about that, I was told that the Whitlock was under new management and no longer had off-site check-in. The additional info we received with attached links also did not work - the response: it will work the day of check in!!?? [ps - they were not "live" links, just a series of numbers and letters] It's great to try and streamline operations, but those operations MUST work, and the responses from the team must make sense!!!"
The Red Lion Inn
10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
More cheap accommodation in Hillsdale

FairBridge Inn Express
16 Cheshire Road Pittsfield MA
NZ$111
26 Aug - 27 Aug
includes taxes & fees

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
NZ$148
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (903 reviews)

Quality Inn Great Barrington
372 Main Street Great Barrington MA
NZ$173
13 Sept - 14 Sept
includes taxes & fees

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
NZ$237
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (170 reviews)

The Yankee Inn
461 Pittsfield Rd Lenox MA
NZ$295
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,018 reviews)

Pocketbook Hotel and Bath
549 Washington Street Hudson NY
NZ$465
31 Aug - 1 Sept
includes taxes & fees
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