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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

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

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (381)
"A positively delightful B&B in a beautiful town. "
The price is AED 386
AED 444 total
includes taxes & fees
5 Jun - 6 Jun
Locust Tree Bed and Breakfast LLC
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, (1000)
"The Inn was beautiful and the staff were knowledgeable and friendly "
The price is AED 473
AED 672 total
includes taxes & fees
5 Jun - 6 Jun
The Cornell Inn, Lenox & The Berkshires
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (105)
"Excellent and lovely location to stay in Norfolk and the vicinity. The staff were great, efficient and made us feel at home. "
The price is AED 611
AED 702 total
includes taxes & fees
11 Jun - 12 Jun
Blackberry River Inn
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (262)
"Wonderful Location"
Lakehouse Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (472)
"Great historic inn loaded with interesting common areas and furnishings."
The price is AED 663
AED 811 total
includes taxes & fees
17 Jun - 18 Jun
Whistler's Inn Bed & Breakfast
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is AED 988
AED 988 total
includes taxes & fees
5 Jun - 6 Jun
Tanglewood Suites
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (284)
"We shall return!"
The price is AED 937
AED 1,060 total
includes taxes & fees
5 Jun - 6 Jun
Inn at Pine Plains
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (412)
"Nice"
The price is AED 519
AED 569 total
includes taxes & fees
15 Jun - 16 Jun
Shaker Mill Inn
it's a good thing
Terrace/patio

it's a good thing

4.5 star property
8.6 out of 10, Excellent, (14)
"Lovely country home with friendly hosts that were prepared for us and very accommodating. "
The price is AED 551
AED 623 total
includes taxes & fees
5 Jun - 6 Jun
it's a good thing
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (364)
"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. "
The price is AED 698
AED 779 total
includes taxes & fees
5 Jun - 6 Jun
Chambery Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (22)
"Always perfect! "
The price is AED 551
AED 615 total
includes taxes & fees
16 Jun - 17 Jun
Wilder House Berkshires
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (125)
"Very enjoyable comfortable stay"
The price is AED 1,025
AED 1,145 total
includes taxes & fees
5 Jun - 6 Jun
Devonfield Inn B&B
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is AED 621
AED 670 total
includes taxes & fees
10 Jun - 11 Jun
Inn at Silver Maple Farm
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (96)
"We had a lovely stay and hope we can come back soon! "
The price is AED 551
AED 595 total
includes taxes & fees
8 Jun - 9 Jun
Changing Times Boutique Country Lodging
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is AED 763
AED 852 total
includes taxes & fees
5 Jun - 6 Jun
Brook Farm Inn
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
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)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is AED 1,551
AED 1,732 total
includes taxes & fees
5 Jun - 6 Jun
33 Main
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 "
The price is AED 1,125
AED 1,361 total
includes taxes & fees
9 Jun - 10 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
Inn at Kenmore Hall
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 551
AED 760 total
includes taxes & fees
8 Jun - 9 Jun
Private room on secluded 7 acres , access to entire house including patio, porch
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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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. Lakehouse Inn: 14 rooms. 16.8 mi (27.1 km) from the heart of downtown. 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.