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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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 444 total
includes taxes & fees
11 Mar - 12 Mar
Locust Tree Bed and Breakfast LLC

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is AED 551
AED 615 total
includes taxes & fees
11 Mar - 12 Mar
The Berkshire Mountain Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (169 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 509
AED 585 total
includes taxes & fees
11 Mar - 12 Mar
Blackberry River Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is AED 708
AED 791 total
includes taxes & fees
12 Mar - 13 Mar
Wilder House Berkshires

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (294 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 502
AED 589 total
includes taxes & fees
20 Mar - 21 Mar
Lakehouse Inn

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (97 reviews)
"Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast."
United States
Ann
The price is AED 639
AED 714 total
includes taxes & fees
11 Mar - 12 Mar
Granville House

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is AED 490
AED 564 total
includes taxes & fees
11 Mar - 12 Mar
The Cornell Inn, Lenox & The Berkshires

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

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 AED 921
AED 1,080 total
includes taxes & fees
3 Apr - 4 Apr
The Inn at Stockbridge

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is AED 551
AED 617 total
includes taxes & fees
11 Mar - 12 Mar
Changing Times Boutique Country Lodging

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AED 433
AED 475 total
includes taxes & fees
23 Mar - 24 Mar
Shaker Mill Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is AED 547
AED 613 total
includes taxes & fees
16 Mar - 17 Mar
Inn at Silver Maple Farm

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (304 reviews)
"Great stay"
United Kingdom
Katherine
The price is AED 909
AED 1,028 total
includes taxes & fees
11 Mar - 12 Mar
Inn at Pine Plains

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 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,137
AED 1,375 total
includes taxes & fees
23 Mar - 24 Mar
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, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
20 Mar - 21 Mar
Inn at Kenmore Hall

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
Brook Farm Inn

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,615
AED 1,804 total
includes taxes & fees
15 Mar - 16 Mar
33 Main

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 AED 551
AED 748 total
includes taxes & fees
16 Mar - 17 Mar
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 AED 551
AED 748 total
includes taxes & fees
16 Mar - 17 Mar
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

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. Situated 15.8 mi (25.4 km) from the heart of Hillsdale. Lakehouse Inn: 14 rooms. 16.8 mi (27.1 km) from the heart of downtown. Enjoy the free full breakfast and deli. Brook Farm Inn: 15 rooms. Located 17 mi (27.3 km) from the core of Hillsdale. Enjoy the free cooked breakfast and outdoor pool.
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.