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B&B in Hillsdale

Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Dec 7 - Dec 8
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$164 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Blackberry River Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
$195 nightly
The price is $218
Dec 12 - Dec 13
Total with taxes and fees
Lakehouse Inn
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
$155 nightly
The price is $174
Dec 16 - Dec 17
Total with taxes and fees
Wilder House Berkshires
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Dec 7 - Dec 8
Total with taxes and fees
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$276 nightly
The price is $308
Dec 21 - Dec 22
Total with taxes and fees
The Inn at Stockbridge
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
$200 nightly
The price is $223
Jan 1 - Jan 2, 2026
Total with taxes and fees
Granville House
Porch
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
$150 nightly
The price is $168
Dec 7 - Dec 8
Total with taxes and fees
Changing Times Boutique Country Lodging
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
$129 nightly
The price is $144
Dec 8 - Dec 9
Total with taxes and fees
Inn at Silver Maple Farm
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
$172 nightly
The price is $192
Dec 8 - Dec 9
Total with taxes and fees
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, (436)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Shaker Mill Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$450 nightly
The price is $503
Dec 14 - Dec 15
Total with taxes and fees
33 Main
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
$349 nightly
The price is $390
Dec 9 - Dec 10
Total with taxes and fees
Devonfield Inn B&B
Business center
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, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Dec 28 - Dec 29
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
$275 nightly
The price is $311
Dec 7 - Dec 8
Total with taxes and fees
Inn at Pine Plains
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
$219 nightly
The price is $219
Dec 7 - Dec 8
Total with taxes and fees
Tanglewood Suites
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
$340 nightly
The price is $373
Dec 7 - Dec 8
Total with taxes and fees
Inn at Kenmore Hall
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox
$310 nightly
The price is $354
Dec 7 - Dec 8
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Terrace/patio
it's a good thing

it's a good thing

4.5 star property
Clinton Corners
8.0 out of 10, Very Good, (24)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
$141 nightly
The price is $160
Jan 1 - Jan 2, 2026
Total with taxes and fees
it's a good thing
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Hillsdale

Hillsdale B&B information

Number of reviews
3,441
Accommodation
49 B&B
Lowest Price
$117
Highest Price
$503

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 $117 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.

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