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Compare 41 B&B in Hillsdale with updated reviews, rates, and availability.

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great Inn, first time at a Bed and Breakfast and it was more than expected. Would come back. "
The price is AED 448
AED 526 total
includes taxes & fees
19 Feb - 20 Feb
The Cornell Inn, Lenox

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (244)
"Wonderful stay. Very relaxing. Customer experience is a truthful effort for the staff. Tranquility and relaxation are met with 5 star efforts. Thanks to Kurt for describing the impressive and living history of the Berkshires. We will definetly be there again! "
The price is AED 463
AED 543 total
includes taxes & fees
21 Feb - 22 Feb
Lakehouse Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 698
AED 780 total
includes taxes & fees
17 Feb - 18 Feb
Chambery Inn

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (97)
"We spent one night and loved the place. It's a beautiful, stately old inn. Our room was nicely appointed and very comfortable. Lucas made us feel at home, and cooked a marvelous breakfast. We'd highly recommend."
The price is AED 604
AED 694 total
includes taxes & fees
17 Feb - 18 Feb
Blackberry River Inn

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (16)
"Room was very cozy and beautiful. Brad was very helpful and pleasant. The breakfast was delicious. We had a great getaway. Thank you. "
The price is AED 493
AED 551 total
includes taxes & fees
23 Feb - 24 Feb
Wilder House Berkshires

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
17 Feb - 18 Feb
Tanglewood Suites

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (281)
"A charming inn with nice rooms upstairs and downstairs and a variety of cozy public rooms on the ground floor. Very nice, serve-yourself continental breakfast, although no hot food (at least not on our weekend). Well-located near the center of Pine Plains."
The price is AED 937
AED 1,060 total
includes taxes & fees
17 Feb - 18 Feb
Inn at Pine Plains

it's a good thing

4.5 star property
9.6 out of 10, Exceptional, (10)
"Lovely country home with friendly hosts that were prepared for us and very accommodating. "
The price is AED 621
AED 702 total
includes taxes & fees
17 Feb - 18 Feb
it's a good thing

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"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 AED 1,410
AED 1,576 total
includes taxes & fees
24 Feb - 25 Feb
33 Main

Granville House

3.0 star property
10.0 out of 10, Exceptional, (81)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 826
AED 923 total
includes taxes & fees
17 Feb - 18 Feb
Granville House

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (407)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
18 Feb - 19 Feb
Shaker Mill Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is AED 915
AED 1,022 total
includes taxes & fees
24 Feb - 25 Feb
Devonfield Inn B&B

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 1,700
AED 1,899 total
includes taxes & fees
17 Feb - 18 Feb
Brook Farm Inn

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

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (375)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is AED 386
AED 444 total
includes taxes & fees
17 Feb - 18 Feb
Locust Tree Bed and Breakfast LLC

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is AED 547
AED 591 total
includes taxes & fees
2 Mar - 3 Mar
Inn at Silver Maple Farm

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 AED 496
AED 631 total
includes taxes & fees
17 Feb - 18 Feb
Private room on secluded 7 acres , access to entire house including patio, porch

Omega Special Sun thru Thurs 5 day minimum 3 miles away

9.0 out of 10, Wonderful, (6)
"The hosts were very kind and attentive to my needs. This is their home and they made me feel welcome and comfortable. The property is old and has beautiful character. If I'm in this area again, I will definitely see if I can stay here. Lovely people."
Omega Special Sun thru Thurs 5 day minimum 3 miles away

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,559
AED 1,886 total
includes taxes & fees
17 Feb - 18 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (125)
"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 AED 514
AED 582 total
includes taxes & fees
17 Feb - 18 Feb
Jenny's Country Manor
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

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"I had an amazing weekend.! Away from everything."
The price is AED 459
AED 496 total
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Eastern Catskills

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"Great property overlooking Hudson River. Close to Woodstock and Rheinbeck. Very good local restaurants for brunch and dinner. Host was great and responded quickly with all questions "
Hamptons on the Hudson in South Saugerties
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. Chambery Inn: 9 rooms. Situated 16.6 mi (26.7 km) from the heart of Hillsdale. Enjoy the private yard and deli. Wilder House Berkshires: 5 rooms. Located 10 mi (16.2 km) from the core of Hillsdale. Enjoy the free cooked breakfast and unique décor.
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.