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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 49 B&B in Hillsdale with updated reviews, rates, and availability.

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (386)
"A positively delightful B&B in a beautiful town. "
$105 nightly
The price is $121
Jun 29 - Jun 30
Total includes taxes and fees
Locust Tree Bed and Breakfast LLC
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (110)
"Very helpful and friendly staff"
$166 nightly
The price is $191
Jun 30 - Jul 1
Total includes taxes and fees
Blackberry River Inn
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
$164 nightly
The price is $183
Jun 30 - Jul 1
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
$269 nightly
The price is $269
Jun 29 - Jun 30
Total includes taxes and fees
Tanglewood Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (266)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
$235 nightly
The price is $263
Jul 2 - Jul 3
Total includes taxes and fees
Lakehouse Inn
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (286)
"Beautiful place. Accomadating staff. A lovely place to stay"
$255 nightly
The price is $288
Jun 29 - Jun 30
Total includes taxes and fees
Inn at Pine Plains
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (25)
"Always perfect! "
$208 nightly
The price is $233
Jul 10 - Jul 11
Total includes taxes and fees
Wilder House Berkshires
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (86)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
$229 nightly
The price is $247
Jul 1 - Jul 2
Total includes taxes and fees
Inn at Silver Maple Farm
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (413)
"Nice"
$142 nightly
The price is $156
Jun 30 - Jul 1
Total includes taxes and fees
Shaker Mill Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (474)
"All was just as advertised and the family/staff was friendly and helpful. "
$198 nightly
The price is $221
Jun 29 - Jun 30
Total includes taxes and fees
Whistler's Inn Bed & Breakfast
it's a good thing
Terrace/patio

it's a good thing

4.5 star property
8.4 out of 10, Very Good, (16)
"Wonderful stay and wonderful hosts! "
$150 nightly
The price is $170
Jul 5 - Jul 6
Total includes taxes and fees
it's a good thing
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (97)
"We had a lovely stay and hope we can come back soon! "
$175 nightly
The price is $189
Jun 30 - Jul 1
Total includes taxes and fees
Changing Times Boutique Country Lodging
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (365)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
$250 nightly
The price is $279
Jun 29 - Jun 30
Total includes taxes and fees
Chambery Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
$269 nightly
The price is $300
Jun 30 - Jul 1
Total includes taxes and fees
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
$289 nightly
The price is $323
Jun 30 - Jul 1
Total includes taxes and fees
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
$497 nightly
The price is $555
Jul 14 - Jul 15
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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)
"Gracious hosts. I felt like a queen in my cozy bedroom."
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"The paint job could be redone and the stair are a bit hazardous. The bath facilities could be improved."
$140 nightly
The price is $158
Jun 29 - Jun 30
Total includes taxes and fees
Jenny's Country Manor
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

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! "
$455 nightly
The price is $509
Jul 28 - Jul 29
Total includes taxes and fees
33 Main
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
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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Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Hillsdale?
Prices for B&Bs in Hillsdale often vary, but you can find a great deal from $121 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Hillsdale B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Hillsdale?
The best time to book a B&B in Hillsdale is during the vibrant fall months of September and October. This enchanting season attracts travelers who appreciate the beauty of autumn foliage and the tranquil atmosphere that accompanies it. As the leaves change colors, Hillsdale becomes a picturesque retreat superb for leisurely walks and scenic drives.

September typically offers mild temperatures ranging from the low 50s to mid-70s Fahrenheit, creating an ideal environment for outdoor activities. Visitors can enjoy hiking in nearby parks or exploring the charming local shops and cafes, all while soaking in the stunning views of the changing landscape.

For those looking to travel on a budget, October presents an excellent opportunity. The crowds have diminished, allowing for a more intimate experience and the chance to enjoy the area's natural beauty without the hustle and bustle of peak tourist season. It's also a great time for local harvest festivals, where you can savor seasonal treats and discover the flavors of the region.
What is the difference between a Hillsdale B&B and a hotel?
Every Hillsdale B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Hillsdale B&Bs.