Find a Bed and Breakfast in Hillsdale from CA $159

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Our top choices for Hillsdale bed & breakfast

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is CA $143
CA $164 total
includes taxes & fees
May 12 - May 13
Locust Tree Bed and Breakfast LLC

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is CA $195
CA $225 total
includes taxes & fees
May 10 - May 11
Blackberry River Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is CA $247
CA $275 total
includes taxes & fees
May 10 - May 11
Wilder House Berkshires

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 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 $258
CA $288 total
includes taxes & fees
May 12 - May 13
The Berkshire Mountain Inn

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)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is CA $197
CA $227 total
includes taxes & fees
May 26 - May 27
The Cornell Inn, Lenox & The Berkshires

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 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 $233
CA $260 total
includes taxes & fees
May 26 - May 27
Chambery Inn

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (101 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 $273
CA $305 total
includes taxes & fees
May 13 - May 14
Granville House

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is CA $366
CA $409 total
includes taxes & fees
May 12 - May 13
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $358
CA $420 total
includes taxes & fees
May 27 - May 28
The Inn at Stockbridge

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 $348
CA $389 total
includes taxes & fees
May 24 - May 25
Whistler's Inn Bed & Breakfast

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is CA $145
CA $159 total
includes taxes & fees
May 13 - May 14
Shaker Mill Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (105 reviews)
"Very nice hotel."
United States
Erdem
The price is CA $217
CA $243 total
includes taxes & fees
May 18 - May 19
Inn at Silver Maple Farm

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 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 $265
CA $297 total
includes taxes & fees
May 13 - May 14
Changing Times Boutique Country Lodging

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (305 reviews)
"Great stay"
United Kingdom
Katherine
The price is CA $344
CA $390 total
includes taxes & fees
May 11 - May 12
Inn at Pine Plains

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is CA $250
CA $290 total
includes taxes & fees
Jun 2 - Jun 3
Brook Farm Inn

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 $421
CA $510 total
includes taxes & fees
May 27 - May 28
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is CA $579
CA $636 total
includes taxes & fees
May 10 - May 11
Inn at Kenmore Hall

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
8.2 out of 10, Very good, (26 reviews)
"Very kind hosts and a great stay!"
United States
Christal
The price is CA $199
CA $225 total
includes taxes & fees
May 11 - May 12
it's a good thing

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, (30 reviews)
"This place is a museum spotless."
United States
Kris A J.
The price is CA $205
CA $279 total
includes taxes & fees
May 8 - May 9
Private room on secluded 7 acres , access to entire house including patio, porch

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 $204
CA $277 total
includes taxes & fees
May 15 - May 16
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
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

Find out more about Hillsdale

Hillsdale B&B information

Number of reviews
3,135
Accommodation
51 B&B
Lowest Price
CA $159
Highest Price
CA $636

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. Situated 13.4 mi (21.6 km) from the heart of Hillsdale. The Berkshire Mountain Inn: 7 rooms. Located 8.2 mi (13.2 km) from the core of Hillsdale. Enjoy the unique décor and library.
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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