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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Hillsdale

Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (409)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
The price is AED 386
AED 444 total
includes taxes & fees
25 Oct - 26 Oct
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (148)
"A wonderful facility, lovely breakfast and way way more than you would expect in every catagory."
United States
Steve
The price is AED 604
AED 694 total
includes taxes & fees
27 Oct - 28 Oct
Blackberry River Inn
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is AED 672
AED 788 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 469
AED 667 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
Interior
The Red Door B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"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 Red Door B&B
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (370)
"ease of late check in. Super comfortable room."
United States
Mary
Chambery Inn
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (499)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is AED 491
AED 548 total
includes taxes & fees
30 Oct - 31 Oct
Whistler's Inn Bed & Breakfast
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
The price is AED 553
AED 618 total
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
United States
Stephanie
The price is AED 804
AED 898 total
includes taxes & fees
25 Oct - 26 Oct
Granville House
Business center
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
9.2 out of 10, Wonderful, (108)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AED 1,137
AED 1,375 total
includes taxes & fees
9 Nov - 10 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (430)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
The price is AED 408
AED 448 total
includes taxes & fees
4 Nov - 5 Nov
Shaker Mill Inn
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is AED 1,274
AED 1,494 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
Aerial view
Inn at Silver Maple Farm
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (97)
"Great stay, comfortable place"
United States
barry
The price is AED 584
AED 654 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
Brook Farm Inn
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
The price is AED 762
AED 1,118 total
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (132)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Free daily continental breakfast
Inn at Pine Plains
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (296)
"Cozy room with comfy bed close to dining. "
United States
Shela
The price is AED 909
AED 1,028 total
includes taxes & fees
26 Oct - 27 Oct
Inn at Pine Plains
Porch
Changing Times Boutique Country Lodging
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (108)
"Great experience, looking forward to staying again."
United States
Greg
The price is AED 643
AED 720 total
includes taxes & fees
26 Oct - 27 Oct
Changing Times Boutique Country Lodging
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
33 Main
4.0 star property
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,689
AED 1,887 total
includes taxes & fees
24 Nov - 25 Nov
33 Main
Terrace/patio
it's a good thing
it's a good thing
4.5 star property
8.2 out of 10, Very Good, (23)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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 surrounding area: The Cornell Inn, Lenox & The Berkshires: 17.9 mi (28.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. Situated 16.8 mi (27.1 km) from the heart of Hillsdale. Enjoy the free full breakfast and deli. Inn at Pine Plains: 8 rooms. 15.3 mi (24.7 km) from the heart of downtown.Chambery Inn: 9 rooms. Located 16.6 mi (26.7 km) from the core of Hillsdale. Enjoy the private yard 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.