A rural landscape with snow-covered fields, a winding road, and scattered trees.

Find a Bed and Breakfast in Hillsdale from CA $172

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Check prices for these dates

Next weekend
Jul 3 - Jul 5
In two weeks
Jul 10 - Jul 12
In one month
Jul 24 - Jul 26
In two months
Aug 21 - Aug 23

Our top choices for Hillsdale bed & breakfast

Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (424 reviews)
"Below average B&B"
United States
Larry
The price is CA $149
CA $172 total
includes taxes & fees
Jun 30 - Jul 1
Locust Tree Bed and Breakfast LLC
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $232
CA $259 total
includes taxes & fees
Jul 1 - Jul 2
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (189 reviews)
"beautiful inn"
United States
Maura
The price is CA $207
CA $239 total
includes taxes & fees
Jul 7 - Jul 8
Blackberry River Inn
Front of property

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
7.6 out of 10, Good, (29 reviews)
"Nothing like what was advertised."
United States
John
The price is CA $198
CA $224 total
includes taxes & fees
Jul 1 - Jul 2
it's a good thing
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.8 out of 10, Excellent, (8 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is CA $377
CA $421 total
includes taxes & fees
Jul 15 - Jul 16
The Berkshire Mountain Inn
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (118 reviews)
"The place is so authentic and beautiful, the owner is so kind and friendly, and we had really good experience "
United States
Tamir
The price is CA $278
CA $311 total
includes taxes & fees
Jun 28 - Jun 29
Changing Times Boutique Country Lodging
Exterior

Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch
Clinton Corners
8.6 out of 10, Excellent, (32 reviews)
"This place is a museum spotless."
United States
Kris A J.
The price is CA $213
CA $293 total
includes taxes & fees
Jul 21 - Jul 22
Private room on secluded 7 acres , access to entire house including patio, porch
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (307 reviews)
"Great stay"
United Kingdom
Katherine
The price is CA $364
CA $412 total
includes taxes & fees
Jun 28 - Jun 29
Inn at Pine Plains
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (109 reviews)
"Very nice hotel."
United States
Erdem
The price is CA $269
CA $301 total
includes taxes & fees
Jul 8 - Jul 9
Inn at Silver Maple Farm
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is CA $298
CA $342 total
includes taxes & fees
Jun 29 - Jun 30
The Cornell Inn, Lenox & The Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $261
CA $286 total
includes taxes & fees
Jul 8 - Jul 9
Shaker Mill Inn
Exterior

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Clinton Corners
8.2 out of 10, Very good, (11 reviews)
"The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting."
United States
Dawn B.
The price is CA $242
CA $331 total
includes taxes & fees
Jun 30 - Jul 1
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is CA $391
CA $437 total
includes taxes & fees
Jun 29 - Jun 30
Granville House
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is CA $284
CA $318 total
includes taxes & fees
Jun 29 - Jun 30
Whistler's Inn Bed & Breakfast
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (380 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $384
CA $429 total
includes taxes & fees
Jun 30 - Jul 1
Chambery Inn
Suite, Private Bathroom (RedBird Suite) | View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $469
CA $568 total
includes taxes & fees
Jul 21 - Jul 22
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is CA $620
CA $727 total
includes taxes & fees
Jul 21 - Jul 22
The Inn at Stockbridge
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $611
CA $682 total
includes taxes & fees
Jul 15 - Jul 16
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $985
CA $1,101 total
includes taxes & fees
Jul 23 - Jul 24
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (167 reviews)
"Lovely stay!"
United States
Jiacheng
The price is CA $394
CA $451 total
includes taxes & fees
Jun 29 - Jun 30
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.
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Top Hillsdale Hotel Reviews

The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel

8/10 Good
"quirky location, nice room"
arthur 1-night trip
Posted 1 hour ago
The Wick, Hudson, A Tribute Portfolio Hotel

Find out more about Hillsdale

Hillsdale B&B information

Number of reviews
3,297
Accommodation
52 B&B
Lowest Price
CA $172
Highest Price
CA $1,101

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 & The Berkshires: 17.9 mi (28.8 km) from the heart of Hillsdale. Enjoy the free full breakfast and unique décor. Locust Tree Bed and Breakfast LLC: 7 rooms. 15.8 mi (25.4 km) from the downtown core. Shaker Mill Inn: 9 rooms. 13.4 mi (21.6 km) from the heart of downtown.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.

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