Find a Bed and Breakfast in Hillsdale from CA $135

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

Browse Select Hillsdale B&B

The Cornell Inn, Lenox
Porch

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1002)
"The weather played a part - our room was accessed by a set of outside stairs, and the weather was cold enough to make them a bit perilous. The staff did its best to attend to it."
The price is CA $135
CA $207 total
includes taxes & fees
Mar 3 - Mar 4
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (247)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is CA $182
CA $213 total
includes taxes & fees
Mar 1 - Mar 2
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
Mar 2 - Mar 3
Chambery Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (98)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is CA $236
CA $271 total
includes taxes & fees
Mar 6 - Mar 7
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3

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 CA $213
CA $238 total
includes taxes & fees
Mar 9 - Mar 10
Wilder House Berkshires
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
Mar 7 - Mar 8
Tanglewood Suites
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (281)
"It was a nice getaway."
The price is CA $366
CA $414 total
includes taxes & fees
Mar 3 - Mar 4
Inn at Pine Plains
it's a good thing
Terrace/patio

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 CA $242
CA $274 total
includes taxes & fees
Mar 9 - Mar 10
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, (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 CA $544
CA $608 total
includes taxes & fees
Mar 6 - Mar 7
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 $325
CA $363 total
includes taxes & fees
Mar 10 - Mar 11
Granville House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (408)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is CA $208
CA $228 total
includes taxes & fees
Mar 9 - Mar 10
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, (122)
"Beautiful property, great service "
The price is CA $357
CA $399 total
includes taxes & fees
Mar 4 - Mar 5
Devonfield Inn B&B
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (150)
"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 $274
CA $307 total
includes taxes & fees
Mar 3 - Mar 4
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, (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 CA $151
CA $173 total
includes taxes & fees
Mar 3 - Mar 4
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, (81)
"Everything "
The price is CA $142
CA $153 total
includes taxes & fees
Mar 3 - Mar 4
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
Mar 2 - Mar 3
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 Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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 CA $609
CA $736 total
includes taxes & fees
Mar 18 - Mar 19
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Jenny's Country Manor
Interior

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 CA $201
CA $227 total
includes taxes & fees
Mar 3 - Mar 4
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.
Don't see what you're looking for?
See all available properties in Hillsdale
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Hillsdale

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is CA $253
CA $273 total
includes taxes & fees
Mar 11 - Mar 12
Postcard Cabins Eastern Catskills
The Ponds at Foxhollow
Property grounds

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
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
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. 16.6 mi (26.7 km) from the heart of downtown. 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.