Find a Bed and Breakfast in Hillsdale from CA $151

  • 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

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)
"the staff was great. rooms where clean there is a bar on site & a bottle of red wine complimentary in the room. a lot in the area unfortunately it was too cold to enjoy a lot of of it"
The price is CA $175
CA $205 total
includes taxes & fees
Jan 21 - Jan 22, 2025
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"This is the most pleasant and comfortable experience I’ve ever had in any hotel. The staff and amenities were outstanding. "
The price is CA $181
CA $212 total
includes taxes & fees
Dec 30 - Dec 31
Lakehouse 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 6 - Jan 7, 2025
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (373)
"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
Dec 26 - Dec 27
Locust Tree Bed and Breakfast LLC
Wilder House Berkshires
Wilder House Berkshires Room 3

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 CA $173
CA $194 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Wilder House Berkshires
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (78)
"Wonderful stay. Charming inn with a virtual library of books for every interest. Terrific breakfast. Will definitely return."
The price is CA $287
CA $321 total
includes taxes & fees
Dec 26 - Dec 27
Granville House
Inn at Pine Plains
Free daily continental breakfast

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 CA $366
CA $410 total
includes taxes & fees
Dec 30 - Dec 31
Inn at Pine Plains
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is CA $273
CA $305 total
includes taxes & fees
Dec 26 - Dec 27
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is CA $151
CA $165 total
includes taxes & fees
Jan 5 - Jan 6, 2025
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, (119)
"Great location "
The price is CA $429
CA $479 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Devonfield Inn B&B
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 $523
CA $584 total
includes taxes & fees
Jan 20 - Jan 21, 2025
33 Main
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 $214
CA $231 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Inn at Silver Maple Farm
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
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 4 - Jan 5, 2025
Tanglewood Suites
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
it's a good thing
Terrace/patio

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 CA $202
CA $227 total
includes taxes & fees
Dec 27 - Dec 28
it's a good thing
Jenny's Country Manor
Miscellaneous

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (124)
"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 $225 total
includes taxes & fees
Dec 26 - Dec 27
Jenny's Country Manor
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 $247 total
includes taxes & fees
Jan 1 - Jan 2, 2025
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
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 $329
CA $367 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Brook Farm Inn
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

Micosta Leisure Inn
Balcony

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 CA $187
CA $201 total
includes taxes & fees
Jan 10 - Jan 11, 2025
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'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 CA $179
CA $208 total
includes taxes & fees
Jan 5 - Jan 6, 2025
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is CA $210
CA $321 total
includes taxes & fees
Dec 30 - Dec 31
Berkshire Village Carriage House - Super Private!!
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.