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Compare 42 B&B in Hillsdale with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1035)
"We were greeted warmly upon arrival with hot beverages and brownies. There were bakery items available all during our stay, and the property features a quaint little bar with many offerings. The breakfast was served in a bright and very well-appointed room with a fireplace and the staff were very friendly and attentive. The food was very nicely presented and delicious. This is a wonderful bed and breakfast at a very affordable price. Will definitely return. "
The price is SAR 458
SAR 537 total
includes taxes & fees
4 Dec - 5 Dec
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is SAR 503
SAR 590 total
includes taxes & fees
23 Nov - 24 Nov
Lakehouse Inn
Blackberry River Inn
Breakfast meal
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (91)
"The room with bathroom was very comfortable and clean. The property was extensive and well maintained. Breakfast choices were extensive and our choices were delicious and cooked by Lucas."
The price is SAR 589
SAR 661 total
includes taxes & fees
25 Nov - 26 Nov
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Exterior
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (367)
"Nice room at reasonable price with breakfast included. "
The price is SAR 394
SAR 453 total
includes taxes & fees
23 Nov - 24 Nov
Locust Tree Bed and Breakfast LLC
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is SAR 713
SAR 797 total
includes taxes & fees
24 Nov - 25 Nov
Chambery Inn
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
The price is SAR 487
SAR 615 total
includes taxes & fees
25 Nov - 26 Nov
Whistler's Inn Bed & Breakfast
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (400)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is SAR 544
SAR 597 total
includes taxes & fees
24 Nov - 25 Nov
Shaker Mill Inn
Inn at Pine Plains
Breakfast area
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (278)
"Ideal version of a New England inn. "
The price is SAR 957
SAR 1,074 total
includes taxes & fees
26 Nov - 27 Nov
Inn at Pine Plains
it's a good thing
Exterior
it's a good thing
4.5 star property
9.6 out of 10, Exceptional, (8)
"There is a tiny little wooden bridge at the entrance of the driveway and the mailbox is on the opposite side of the road from the house. A doe was keeping watch on the mailbox when we arrived after dark. And check out the night sky!"
The price is SAR 436
SAR 483 total
includes taxes & fees
24 Nov - 25 Nov
it's a good thing
Inn at Silver Maple Farm
Front of property
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (79)
"Everything "
The price is SAR 597
SAR 645 total
includes taxes & fees
25 Nov - 26 Nov
Inn at Silver Maple Farm
Wilder House Berkshires
Living area
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (10)
"Great place, very clean, hospitable and designed with impeccable taste. "
The price is SAR 505
SAR 565 total
includes taxes & fees
24 Nov - 25 Nov
Wilder House Berkshires
Changing Times Boutique Country Lodging
Front of property
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (92)
"The stay was great. The host baked delicious muffins for breakfast and everything was clean "
The price is SAR 563
SAR 608 total
includes taxes & fees
24 Nov - 25 Nov
Changing Times Boutique Country Lodging
Granville House
Room
Granville House
3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is SAR 751
SAR 839 total
includes taxes & fees
24 Nov - 25 Nov
Granville House
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is SAR 1,314
SAR 1,467 total
includes taxes & fees
4 Dec - 5 Dec
33 Main
Jenny's Country Manor
Miscellaneous
Jenny's Country Manor
2.0 star property
7.6 out of 10, Good, (123)
"The manager was very amenable to changing our room due to a complaint about a problem we had. And was sincerely concerned. They have a very nice light breakfast on Saturday mornings. "
The price is SAR 526
SAR 589 total
includes taxes & fees
24 Nov - 25 Nov
Jenny's Country Manor
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is SAR 728
SAR 814 total
includes taxes & fees
29 Nov - 30 Nov
Brook Farm Inn
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Exterior
Omega Special Sun thru Thurs 5 day minimum 3 miles away
9.6 out of 10, Exceptional, (11)
"Beautiful, quiet, comfortable accommodation in gorgeous surroundings. Hosts are kind and helpful. Enjoyed our stay!"
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (117)
"Arrived Friday to see a Tanglewood concert. Inn provided lovely afternoon cocktails and appetizers with piano music. Saturday hosts sponsored garden concert with local artists - really nice after morning hike to water fall and early afternoon golf. Yummy Morning breakfast each day. Central to Stonebridge and Lenox. Hosts very knowledgeable "
The price is SAR 1,047
SAR 1,170 total
includes taxes & fees
23 Nov - 24 Nov
Devonfield Inn B&B
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Private room on secluded 7 acres , access to entire house including patio, porch
Exterior
Private room on secluded 7 acres , access to entire house including patio, porch
8.8 out of 10, Excellent, (24)
"This is a lovely room in a quaint historic large home just a few miles down the road from the Omega Institute. I stayed there b/c Omega had no more housing. Lynn was a delightful and accommodating hostess. Would definitely stay again."
The price is SAR 563
SAR 711 total
includes taxes & fees
24 Nov - 25 Nov
Private room on secluded 7 acres , access to entire house including patio, porch
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.
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Other property types in Hillsdale

Micosta Leisure Inn
Terrace/patio
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is SAR 434
SAR 468 total
includes taxes & fees
30 Nov - 1 Dec
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 537
SAR 830 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Cabin Overlooking Chloe's Lake
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.2 out of 10, Very Good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is SAR 469
SAR 544 total
includes taxes & fees
22 Dec - 23 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.

Frequently asked questions

Searching for B&Bs in Hillsdale?
If you want to find a place to stay with a small number of rooms and an intimate environment, a B&B may be the perfect thing for your vacation to Hillsdale. If you’re looking to hit the slopes on your trip to Hillsdale, Catamount Ski Area is worth a visit.
Why consider a B&B over a traditional hotel room?
With attentive service, opportunities to mingle with other guests, and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the best bed and breakfasts in Hillsdale?
Here are some well-liked B&Bs in the area: The Cornell Inn, Lenox: 17.9 mi (28.8 km) from the heart of Hillsdale. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 16.8 mi (27.1 km) from the downtown core. Enjoy the free full breakfast and deli. Locust Tree Bed and Breakfast LLC: 7 rooms. 15.8 mi (25.4 km) from the heart of downtown.Shaker Mill Inn: 9 rooms. Located 13.4 mi (21.6 km) from the core of Hillsdale.
What's the best time of year to book my B&B in Hillsdale?
When you’re dreaming of a stay in Hillsdale, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Hillsdale?
Spend some time exploring Copake Lake and Mosquito Island if you’re hoping to see some of the area’s natural features. You might put Catamount Aerial Adventure Park and Catamount Ski Area on your list if you want to see more of the area.
How can I get to and around Hillsdale?
Planning your excursions in and around Hillsdale is easier with these transportation options. Fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) away from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.