A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

Our top choices for Hillsdale bed & breakfast

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (67 reviews)
"Perfect little b&b."
United States
Mark
The price is AED 758
AED 847 total
includes taxes & fees
25 Oct - 26 Oct
Wilder House Berkshires
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

2. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
The price is AED 735
AED 823 total
includes taxes & fees
5 Oct - 6 Oct
Changing Times Boutique Country Lodging
A dining table with pastries, a coffee pot, and a vase of sunflowers.

3. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 826
AED 923 total
includes taxes & fees
1 Nov - 2 Nov
Granville House
A red building with a sign reading "Shaker Mill Inn."

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 489
AED 536 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

5. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (222 reviews)
"Great breakfast"
United States
Brian
The price is AED 551
AED 634 total
includes taxes & fees
4 Oct - 5 Oct
Blackberry River Inn
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

6. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (317 reviews)
"Great place! Comfy and charming!!"
United States
Mary
The price is AED 970
AED 1,097 total
includes taxes & fees
14 Oct - 15 Oct
Inn at Pine Plains
A snow-covered outdoor area with a patio, seating, and a covered dining area.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A two-story house with a brick entrance and a white facade.

8. 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, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,403
AED 1,697 total
includes taxes & fees
1 Nov - 2 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

9. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"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
The price is AED 574
AED 949 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
Front of property

10. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AED 1,340
AED 1,571 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

11. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 859
AED 963 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Silver Maple Farm
A garden with a white gazebo, a brick pathway, and various plants and flowers.

12. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 579
AED 646 total
includes taxes & fees
4 Oct - 5 Oct
Whistler's Inn Bed & Breakfast
A two-story building with a sign reading "Chambéry Inn".

13. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AED 962
AED 1,074 total
includes taxes & fees
1 Nov - 2 Nov
Chambery Inn
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

14. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (450 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is AED 386
AED 444 total
includes taxes & fees
4 Oct - 5 Oct
Locust Tree Bed and Breakfast LLC
A large, two-story house with a well-maintained lawn and a fence.

15. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is AED 1,392
AED 1,555 total
includes taxes & fees
1 Nov - 2 Nov
Devonfield Inn B&B
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

16. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 909
AED 1,182 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

17. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AED 812
AED 937 total
includes taxes & fees
21 Oct - 22 Oct
Brook Farm Inn
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

18. 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, (33 reviews)
"Wonderful hosts in a quaint home in a lovely spot."
United States
Sharen B.
The price is AED 496
AED 686 total
includes taxes & fees
5 Oct - 6 Oct
Private room on secluded 7 acres , access to entire house including patio, porch
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

19. 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
7.8 out of 10, Good, (12 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 562
AED 769 total
includes taxes & fees
11 Oct - 12 Oct
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

20. it's a good thing

it's a good thing
3.0 star property
Clinton Corners
7.8 out of 10, Good, (35 reviews)
"The warmth of the owners!"
United States
Evangelia
The price is AED 618
AED 700 total
includes taxes & fees
5 Oct - 6 Oct
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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Clean, big rooms!"
Mark 1-night trip
Posted 9 hours ago
Howard Johnson by Wyndham Lenox

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. Inn at Silver Maple Farm: 11 rooms. 16.8 mi (27.1 km) from the heart of downtown. Enjoy the free buffet breakfast and designer toiletries. Shaker Mill Inn: 9 rooms. Located 13.4 mi (21.6 km) from the core of Hillsdale.
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.

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