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Check prices for these dates

Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9
In one month
Nov 21 - Nov 23
In two months
Dec 19 - Dec 21

B&B in Hillsdale

Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (406)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
$105 nightly
The price is $121
Oct 21 - Oct 22
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (147)
"A wonderful facility, lovely breakfast and way way more than you would expect in every catagory."
United States
Steve
$164 nightly
The price is $189
Oct 21 - Oct 22
Total with taxes and fees
Blackberry River Inn
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
$196 nightly
The price is $219
Oct 21 - Oct 22
Total with taxes and fees
Lakehouse Inn
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1010)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
$163 nightly
The price is $182
Oct 26 - Oct 27
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Interior
The Red Door B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
$270 nightly
The price is $302
Oct 27 - Oct 28
Total with taxes and fees
The Red Door B&B
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
United States
Mary
$190 nightly
The price is $212
Oct 26 - Oct 27
Total with taxes and fees
Chambery Inn
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (36)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
$155 nightly
The price is $174
Oct 27 - Oct 28
Total with taxes and fees
Wilder House Berkshires
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (497)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
$170 nightly
The price is $190
Oct 21 - Oct 22
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
United States
Stephanie
$219 nightly
The price is $245
Oct 26 - Oct 27
Total with taxes and fees
Granville House
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
$364 nightly
The price is $407
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Stockbridge
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (430)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
$122 nightly
The price is $134
Nov 4 - Nov 5
Total with taxes and fees
Shaker Mill Inn
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
9.2 out of 10, Wonderful, (107)
"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
$335 nightly
The price is $374
Nov 3 - Nov 4
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Porch
Changing Times Boutique Country Lodging
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (108)
"Great experience, looking forward to staying again."
United States
Greg
$175 nightly
The price is $196
Oct 21 - Oct 22
Total with taxes and fees
Changing Times Boutique Country Lodging
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
$170 nightly
The price is $190
Oct 22 - Oct 23
Total with taxes and fees
Brook Farm Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
33 Main
4.0 star property
10.0 out of 10, Exceptional, (73)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$492 nightly
The price is $550
Nov 19 - Nov 20
Total with taxes and fees
33 Main
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (132)
"The inn has an excellent location and amenities."
United States
Christopher
$379 nightly
The price is $423
Nov 4 - Nov 5
Total with taxes and fees
Devonfield Inn B&B
Free daily continental breakfast
Inn at Pine Plains
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (296)
"Cozy room with comfy bed close to dining. "
United States
Shela
$275 nightly
The price is $311
Oct 21 - Oct 22
Total with taxes and fees
Inn at Pine Plains
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
$237 nightly
The price is $304
Oct 26 - Oct 27
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Aerial view
Inn at Silver Maple Farm
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (96)
"Great stay, comfortable place"
United States
barry
$189 nightly
The price is $212
Nov 2 - Nov 3
Total with taxes and fees
Inn at Silver Maple Farm
Terrace/patio
it's a good thing
it's a good thing
4.5 star property
8.2 out of 10, Very Good, (23)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
$146 nightly
The price is $166
Oct 21 - Oct 22
Total with taxes and fees
it's a good thing
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Kitchen and parking both very good"
Joseph 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale B&B information

Number of reviews
3,680
Accommodation
49 B&B
Lowest Price
$121
Highest Price
$550

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.

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