Search B&B in Hillsdale

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
Front of property – evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is HK$2,022
HK$2,259 total
includes taxes & fees
19 May - 20 May
Devonfield Inn B&B
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is HK$3,023
HK$3,377 total
includes taxes & fees
27 May - 28 May
33 Main
Interior detail
Granville House
4.0 star property
10.0 out of 10, Exceptional, (69)
"It is a very nice location and we felt very comfortable during our stay . The included breakfast was delicious and we felt like royalty during our stay. "
The price is HK$1,562
HK$1,744 total
includes taxes & fees
21 May - 22 May
Granville House
Save an average of 15% on thousands of hotels when you're signed in
Premium bedding, individually decorated, individually furnished, desk
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (84)
"It was comfortable"
The price is HK$1,015
HK$1,096 total
includes taxes & fees
22 May - 23 May
Changing Times Boutique Country Lodging
Property grounds
Private Guest Area in Plant Based Bed and Breakfast
10.0 out of 10, Exceptional, (5)
"Adorable, beautifully decorated, super clean house. Friendly, attentive owner., sweet dog and a delicious breakfast - what more could you ask. Our room was lovely and exactly as pictured. Would definitely return! Thanks Emily!"
Private Guest Area in Plant Based Bed and Breakfast
Lobby
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
1 bedroom, desk, iron/ironing board, WiFi
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is HK$3,115
HK$3,977 total
includes taxes & fees
20 May - 21 May
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Free daily continental breakfast
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (258)
"Lovely overnight stay. Room was beautiful and very comfortable. Breakfast consisted of a nice selection of homemade bread and muffins - and humus (so yummy). Staff is super friendly and made sure to engage with everyone. Would definitely stay here again. "
The price is HK$1,757
HK$1,970 total
includes taxes & fees
19 May - 20 May
Inn at Pine Plains
Aerial view
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (67)
"I had a wonderful stay here with my sister. I would definitely go back next time i am in the area"
The price is HK$1,163
HK$1,256 total
includes taxes & fees
21 May - 22 May
Inn at Silver Maple Farm
Exterior
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is HK$2,335
HK$2,957 total
includes taxes & fees
21 May - 22 May
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Cozy, comfortable, feels like you are staying at someone’s home that you love, but, lol with privacy! Breakfast is fabulous and eggs are made to order!"
The price is HK$1,417
HK$1,630 total
includes taxes & fees
20 May - 21 May
Blackberry River Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is HK$1,054
HK$1,236 total
includes taxes & fees
19 May - 20 May
Lakehouse Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (382)
"Perfect little country inn tucked in the Berkshires, convenient to the highway but off the beaten path on a quiet rural road. Our first floor suite was spacious, inviting, comfortable, and clearly designed with care. Would definitely return next time we’re in the area. "
The price is HK$1,070
HK$1,174 total
includes taxes & fees
29 May - 30 May
Shaker Mill Inn
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is HK$1,868
HK$2,086 total
includes taxes & fees
28 May - 29 May
Chambery Inn
Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (96)
"Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. "
The price is HK$2,538
HK$2,834 total
includes taxes & fees
17 May - 18 May
The Barrington
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"This is a charming and very pleasant place to stay."
The price is HK$1,108
HK$1,238 total
includes taxes & fees
20 May - 21 May
Brook Farm Inn
View from property
Private bed& bath on secluded land centrally located 7 miles to rhinebeck
9.4 out of 10, Exceptional, (10)
"We had a great stay up and away from Rt 9. Lynn made us feel right at home. We started each day with the coffee perc she setup for before us (a feat: we wake up early). The golden spud cafe being right down the road was quite nice to have access to."
The price is HK$859
HK$1,132 total
includes taxes & fees
11 Jun - 12 Jun
Private bed& bath on secluded land centrally located 7 miles to rhinebeck
Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is HK$2,820
HK$3,412 total
includes taxes & fees
17 May - 18 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (321)
"Great B&B … everything is easy, clean, friendly owners, great breakfast! "
The price is HK$820
HK$943 total
includes taxes & fees
19 May - 20 May
Locust Tree Bed and Breakfast LLC
Don't see what you're looking for?
See all available properties in Hillsdale
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.

Other property types in Hillsdale

7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
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.

Hillsdale B&B information

Number of reviews
2,988
Accommodation
46 B&B
Lowest Price
HK$820
Highest Price
HK$3,023

Frequently asked questions

Searching for B&Bs in Hillsdale?
If you’d like to find somewhere to stay with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be just the right fit for your holiday to Hillsdale. If you’re looking to hit the slopes on your trip to Hillsdale, Catamount Ski Area is worth a visit.
Why would you choose B&Bs instead of traditional hotels?
With attentive service, opportunities to meet other guests and tasty breakfasts, B&Bs offer a truly one-of-a-kind environment.
What's the best time of year to book my B&B in Hillsdale?
When you’re dreaming of a escape to Hillsdale, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Hillsdale?
When you want to explore some things to do in town, Catamount Aerial Adventure Park and Catamount Ski Area are some notable sights to visit. You should put Hillsdale Town Hall and Community Library 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. Otherwise, you can search for flights to 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 to rent a car for your trip.

Recent Hotel Reviews in Hillsdale
Expedia verified reviews