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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 40 B&B in Hillsdale with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"This is my favorite place to stay in Lee! The room is cozy and the complimentary breakfast is delicious! The staff are professional and courteous. I will be back."
The price is AED 455
AED 652 total
includes taxes & fees
10 Apr - 11 Apr
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (254)
"We had a great stay at The Lakehouse Inn. Upon arrival we were greeted with a beverage and brownies. Our room was lovely, the new gas fireplace was a bonus. And the breakfast was out of this world! Service was fantastic from everyone involved, especially our breakfast server Kathleen. We would definitely recommend a stay here."
Lakehouse Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (99)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is AED 611
AED 702 total
includes taxes & fees
5 May - 6 May
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (18)
"I’m a returning guest. The house is always charming, welcoming, comfortable and clean! The owner is very accommodating. "
The price is AED 562
AED 628 total
includes taxes & fees
17 Apr - 18 Apr
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (376)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is AED 386
AED 444 total
includes taxes & fees
10 Apr - 11 Apr
Locust Tree Bed and Breakfast LLC
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (409)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is AED 533
AED 584 total
includes taxes & fees
13 Apr - 14 Apr
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 881
AED 985 total
includes taxes & fees
11 Apr - 12 Apr
Chambery Inn
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! "
The price is AED 1,441
AED 1,610 total
includes taxes & fees
10 Apr - 11 Apr
33 Main
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (281)
"A charming inn with nice rooms upstairs and downstairs and a variety of cozy public rooms on the ground floor. Very nice, serve-yourself continental breakfast, although no hot food (at least not on our weekend). Well-located near the center of Pine Plains."
The price is AED 937
AED 1,060 total
includes taxes & fees
10 Apr - 11 Apr
Inn at Pine Plains
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 741
AED 827 total
includes taxes & fees
10 Apr - 11 Apr
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, (123)
"Fantastic in every way! We highly recommend the inn for the warm atmosphere, superb service and lovely facilities. First rate!"
The price is AED 915
AED 1,022 total
includes taxes & fees
10 Apr - 11 Apr
Devonfield Inn B&B
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
The price is AED 601
AED 741 total
includes taxes & fees
1 May - 2 May
Whistler's Inn Bed & Breakfast
it's a good thing
Terrace/patio

it's a good thing

4.5 star property
9.6 out of 10, Exceptional, (10)
"Lovely country home with friendly hosts that were prepared for us and very accommodating. "
The price is AED 621
AED 702 total
includes taxes & fees
10 Apr - 11 Apr
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)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,559
AED 1,885 total
includes taxes & fees
10 Apr - 11 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Jenny's Country Manor
Interior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (126)
"The manager was very amenable to changing our room due to a complaint about a problem we had. And was sincerely concerned. They have a very nice light breakfast on Saturday mornings. "
The price is AED 514
AED 582 total
includes taxes & fees
10 Apr - 11 Apr
Jenny's Country Manor
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)
"Beautiful, quiet, comfortable accommodation in gorgeous surroundings. Hosts are kind and helpful. Enjoyed our stay!"
Omega Special Sun thru Thurs 5 day minimum 3 miles away
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (82)
"The Inn was welcoming and comfortable with homemade cookies waiting for us at check in! The decor was especially inviting, we loved it! The staff that took our breakfast order, was equally warm, inviting, and accommodating. "
The price is AED 547
AED 591 total
includes taxes & fees
10 Apr - 11 Apr
Inn at Silver Maple Farm
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Private room on secluded 7 acres , access to entire house including patio, porch
Property grounds

Private room on secluded 7 acres , access to entire house including patio, porch

8.8 out of 10, Excellent, (24)
"This is a lovely room in a quaint historic large home just a few miles down the road from the Omega Institute. I stayed there b/c Omega had no more housing. Lynn was a delightful and accommodating hostess. Would definitely stay again."
The price is AED 496
AED 686 total
includes taxes & fees
10 Apr - 11 Apr
Private room on secluded 7 acres , access to entire house including patio, porch
Granville House
Interior detail

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!"
The price is AED 731
AED 816 total
includes taxes & fees
20 Apr - 21 Apr
Granville House
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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Other property types in Hillsdale

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Fridge, oven, stovetop, dishwasher

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

10.0 out of 10, Exceptional, (11)
"We had our family Thanksgiving at this home and it was a great time. Enough space to cook a Thanksgiving meal, have a baking contest, play board games, and relax. The bedrooms were comfortable and everyone commented on how well they slept. More than enough bathrooms and showers with hot water for six people. Close to Great Barrington and Stockbridge for some small town vibes. Overall a great stay!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (7)
"We always live these cabins & we've been coming for years!"
The price is AED 643
AED 694 total
includes taxes & fees
10 Apr - 11 Apr
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is AED 477
AED 515 total
includes taxes & fees
22 Apr - 23 Apr
Micosta Leisure 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.

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. 15.8 mi (25.4 km) from the downtown core. Chambery Inn: 9 rooms. 16.6 mi (26.7 km) from the heart of downtown. Enjoy the private yard and deli. Lakehouse Inn: 14 rooms. Located 16.8 mi (27.1 km) from the core of Hillsdale. Enjoy the free full breakfast and deli.
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.