Book Hillsdale Bed & Breakfast

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Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

B&B in Hillsdale

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (399)
"A positively delightful B&B in a beautiful town. "
$105 nightly
The price is $121
Aug 18 - Aug 19
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, (125)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
$164 nightly
The price is $189
Sep 2 - Sep 3
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)
"Lovely place. Excellent staff, Wonderful breakfast."
$163 nightly
The price is $182
Sep 1 - Sep 2
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires
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, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
$173 nightly
The price is $193
Sep 9 - Sep 10
Total includes taxes and fees
Wilder House Berkshires
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (420)
"Very casual and easy check in and out; lovely and substantial breakfast"
$182 nightly
The price is $200
Aug 19 - Aug 20
Total includes taxes and fees
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"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
Aug 17 - Aug 18
Total includes taxes and fees
Chambery Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
$309 nightly
The price is $345
Sep 1 - Sep 2
Total includes taxes and fees
Devonfield Inn B&B
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
$249 nightly
The price is $278
Aug 20 - Aug 21
Total includes taxes and fees
Granville House
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
$209 nightly
The price is $234
Sep 2 - Sep 3
Total includes taxes and fees
Inn at Silver Maple Farm
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
$193 nightly
The price is $215
Aug 17 - Aug 18
Total includes taxes and fees
Whistler's Inn Bed & Breakfast
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, (156)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
$249 nightly
The price is $278
Sep 1 - Sep 2
Total includes taxes and fees
Brook Farm Inn
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
7.4 out of 10, Good, (18)
"Made a Friday night reservation for their 2BR suite in August. When we arrived at the location listed on Expedia, we found ourselves in a residential neighborhood with no "Tanglewood Suites" in sight. I had emailed in advance for clarification on the location but didn't get a reply. We called the place and the proprietor said there was no record of a reservation and that she never rents for one night only. We were left high and dry with no reasonably priced play to stay in the area. "
$269 nightly
The price is $269
Aug 17 - Aug 18
Total includes taxes and fees
Tanglewood Suites
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (102)
"The b and b is charming and comfortable. Loretta was extremely welcoming and accommodating."
$175 nightly
The price is $196
Aug 17 - Aug 18
Total includes taxes and fees
Changing Times Boutique Country Lodging
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (288)
"Beautiful place. Accomadating staff. A lovely place to stay"
$255 nightly
The price is $288
Aug 17 - Aug 18
Total includes taxes and fees
Inn at Pine Plains
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
Aug 17 - Aug 18
Total includes taxes and fees
Jenny's Country Manor
it's a good thing
Terrace/patio

it's a good thing

4.5 star property
8.6 out of 10, Excellent, (18)
"Wonderful stay and wonderful hosts! "
$146 nightly
The price is $166
Aug 17 - Aug 18
Total includes taxes and fees
it's a good thing
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 "
$447 nightly
The price is $500
Aug 31 - Sep 1
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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! "
$600 nightly
The price is $671
Aug 18 - Aug 19
Total includes taxes and fees
33 Main
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Property grounds

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

8.2 out of 10, Very Good, (11)
"Quiet and quaint rustic charm. Hosts were friendly and accommodating."
$172 nightly
The price is $195
Aug 17 - Aug 18
Total includes taxes and fees
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

$234 nightly
The price is $301
Sep 1 - Sep 2
Total includes taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Bed was comfortable, breakfast options very good. Intermittent WiFi connections. "
Alan 4-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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.