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

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Hillsdale bed & breakfast

A dining table with pastries, a coffee pot, and a vase of sunflowers.

1. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is CA $356
CA $397 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
Interior detail

2. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is CA $243
CA $271 total
includes taxes & fees
Oct 27 - Oct 28
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.

3. 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 CA $280
CA $314 total
includes taxes & fees
Oct 27 - Oct 28
Changing Times Boutique Country Lodging
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, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is CA $169
CA $186 total
includes taxes & fees
Nov 2 - Nov 3
Shaker Mill Inn
A two-story house with a brick entrance and a white facade.

5. 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, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $476
CA $576 total
includes taxes & fees
Nov 7 - Nov 8
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A snow-covered outdoor area with a patio, seating, and a covered dining area.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
United States
Sandra
The price is CA $215
CA $246 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

7. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (318 reviews)
"good location/ walkable to down town !"
United States
teresina
The price is CA $385
CA $436 total
includes taxes & fees
Oct 27 - Oct 28
Inn at Pine Plains
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

8. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is CA $258
CA $289 total
includes taxes & fees
Nov 22 - Nov 23
Inn at Silver Maple Farm
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

9. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (243 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is CA $245
CA $282 total
includes taxes & fees
Nov 4 - Nov 5
Blackberry River Inn
Front of property

10. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is CA $511
CA $599 total
includes taxes & fees
Nov 12 - Nov 13
The Inn at Stockbridge
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

11. 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 traveller
The price is CA $246
CA $392 total
includes taxes & fees
Oct 26 - Oct 27
The Red Door B&B
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, (520 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is CA $208
CA $232 total
includes taxes & fees
Oct 27 - Oct 28
Whistler's Inn Bed & Breakfast
A large, two-story house with a well-maintained lawn and a fence.

13. 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 CA $517
CA $577 total
includes taxes & fees
Nov 4 - Nov 5
Devonfield Inn B&B
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, (453 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is CA $147
CA $169 total
includes taxes & fees
Oct 25 - Oct 26
Locust Tree Bed and Breakfast LLC
A two-story building with a sign reading "Chambéry Inn".

15. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (389 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 CA $314
CA $351 total
includes taxes & fees
Nov 17 - Nov 18
Chambery Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

16. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is CA $259
CA $300 total
includes taxes & fees
Oct 25 - Oct 26
Brook Farm Inn
A dining room with a wooden table and chairs, a chandelier, and a door with a window.

17. Omega Special 1860s farm house 3 miles away

Omega Special 1860s farm house 3 miles away
Clinton Corners
8.6 out of 10, Excellent, (12 reviews)
"Lynn was incredibly kind, helpful, and friendly. Our stay was very comfortable and centrally located to everywhere we wanted to be. The property was beautiful and scenic, and the home was as cozy and comfortable. She even put out breakfast and coffee for us in the morning, which was very nice! We would absolutely stay again!"
United States
Kenneth P
The price is CA $189
CA $269 total
includes taxes & fees
Oct 25 - Oct 26
Omega Special 1860s farm house 3 miles away
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

18. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $346
CA $454 total
includes taxes & fees
Oct 27 - Oct 28
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

19. 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 CA $189
CA $263 total
includes taxes & fees
Oct 25 - Oct 26
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.

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 CA $251
CA $284 total
includes taxes & fees
Oct 25 - Oct 26
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

Hotel On North

Hotel On North

10/10 Excellent
"Charming hotel, far exceeded expectations. Clean. Well managed. Stayed for a girls weekend and enjoyed the area and surrounding towns. Would highly recommend."
Amie 2-night trip
Posted 8 hours ago
Hotel On North

Find out more about Hillsdale

Hillsdale B&B information

Number of reviews
4,068
Accommodation
52 B&B
Lowest Price
CA $169
Highest Price
CA $599

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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