Find a Bed and Breakfast in Hillsdale from CA $151

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Check prices for these dates

Next weekend
Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
In one month
Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Browse Select Hillsdale B&B

The Cornell Inn, Lenox
Porch

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1001)
"My room was adorable...completely charming and well appointed. I appreciated the phone call with detailed late check-in instructions and when I arrived the property manager walked me to my room. Breakfast was lovely and the staff very friendly. Town a is an easy walk."
The price is CA $175
CA $205 total
includes taxes & fees
Jan 27 - Jan 28
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is CA $181
CA $212 total
includes taxes & fees
Jan 31 - Feb 1
Lakehouse Inn
Chambery Inn
Front of property

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 CA $272
CA $304 total
includes taxes & fees
Jan 30 - Jan 31
Chambery Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (95)
"Very clean. The host was friendly and attentive. Great complimentary breakfast. Clean,quiet and very comfortable. "
The price is CA $225
CA $259 total
includes taxes & fees
Jan 27 - Jan 28
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (14)
"Nice old charming room "
The price is CA $227
CA $253 total
includes taxes & fees
Jan 29 - Jan 30
Wilder House Berkshires
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (280)
"I wanted to find a nice bed-and-breakfast inn-type place to stay at during a brief trip to upstate New York (Dutchess County). The Inn at Pine Plains receives consistently excellent reviews on Expedia so I decided to follow those recommendations. The good reviews are accurate. Plus, there are at least two excellent world-class restaurants within walking distance. "
The price is CA $366
CA $410 total
includes taxes & fees
Jan 27 - Jan 28
Inn at Pine Plains
Tanglewood Suites
2 Bedrooms 1 Bath

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 CA $314
CA $314 total
includes taxes & fees
Jan 27 - Jan 28
Tanglewood Suites
it's a good thing
Terrace/patio

it's a good thing

4.5 star property
9.6 out of 10, Exceptional, (10)
"We needed a place to stay close to Rhinebeck. We found this place "It's a good thing" on Expedia. The hosts were gracious, the beds were comfortable, and the breakfast in the morning was exactly what we wanted. I will certainly consider staying again at this lovely home."
The price is CA $202
CA $227 total
includes taxes & fees
Jan 27 - Jan 28
it's a good thing
33 Main
Luxury Room, 1 King Bed, Bathtub

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 CA $463
CA $518 total
includes taxes & fees
Feb 3 - Feb 4
33 Main
Granville House
Interior detail

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 CA $323
CA $360 total
includes taxes & fees
Jan 27 - Jan 28
Granville House
Shaker Mill Inn
Garden

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 CA $151
CA $165 total
includes taxes & fees
Jan 27 - Jan 28
Shaker Mill Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (121)
"Great location "
The price is CA $400
CA $447 total
includes taxes & fees
Jan 27 - Jan 28
Devonfield Inn B&B
Brook Farm Inn
Front of property

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 CA $248
CA $277 total
includes taxes & fees
Jan 27 - Jan 28
Brook Farm Inn
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Property grounds

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
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (374)
"Very pretty setting and house. Comfortable bed. Nice view Would have liked bottled water available in the room. Breakfast was nice."
The price is CA $151
CA $173 total
includes taxes & fees
Jan 27 - Jan 28
Locust Tree Bed and Breakfast LLC
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is CA $199
CA $215 total
includes taxes & fees
Jan 27 - Jan 28
Inn at Silver Maple Farm
Private room on secluded 7 acres , access to entire house including patio, porch
Property grounds

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 CA $194
CA $246 total
includes taxes & fees
Jan 27 - Jan 28
Private room on secluded 7 acres , access to entire house including patio, porch
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Property grounds

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 Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Property grounds

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...
Whistler's Inn Bed & Breakfast
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 by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is CA $332
CA $370 total
includes taxes & fees
Feb 14 - Feb 15
The Ponds at Foxhollow by Capital Vacations
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Absolutely wonderful. Charming, pristine and cozy for an overnight stay. "
The price is CA $215
CA $327 total
includes taxes & fees
Jan 28 - Jan 29
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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. Locust Tree Bed and Breakfast LLC: 7 rooms. Located 15.8 mi (25.4 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.