Title: Hillsdale B&B: Find the Best Bed and Breakfast from CA $164 | Expedia.ca [Hillsdale Travel Guide](https://expedia.ca/Hillsdale.dx183683)[Hotels in Hillsdale](https://expedia.ca/Hillsdale-Hotels.d183683.Travel-Guide-Hotels)[Vacation Rentals in Hillsdale](https://expedia.ca/Hillsdale-Vacation-Rentals.d183683.Travel-Guide-VacationRentals)[Hillsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsdale.d183683.Car-Rental-Guide)[Hillsdale Vacation Packages](https://expedia.ca/Hillsdale.d183683.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Hillsdale from CA $164 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Hillsdale B&B ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fb8a0016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9fc87fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fd1046f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locust Tree Bed and Breakfast LLC East Canaan 9.0/10 Wonderful (409) "Great breakfast! Had a wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $147 CA $169 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry River Inn Norfolk 9.4/10 Exceptional (151) "A wonderful facility, lovely breakfast and way way more than you would expect in every catagory." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $230 CA $264 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn Lee 9.6/10 Exceptional (287) "Great Views & Hospitality" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $253 CA $297 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/a6853cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn Lee 9.6/10 Exceptional (371) "Beautiful stay. We booked last minute and it was amazing! We were able to book the room with jacuzzi and a fireplace—which made the whole stay so romantic. Will recommend and am planning to visit regularly. Hoping to return in the fall but definitely next spring. This family works hard and takes pride in their Inn and it shows in every inch of the grounds. Loved every minute!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1002) "Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $180 CA $255 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Wilder House Berkshires Room 3](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/8660fa49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/683afd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilder House Berkshires Sheffield 9.8/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Marina CA $222 CA $249 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/c9940794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/0fed38f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pines Duplex Suite | View from room](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/7bcf94fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/6c685368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Silver Maple Farm East Chatham 9.8/10 Exceptional (97) "Great stay, comfortable place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) barry CA $180 CA $202 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/25fee020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/6d6ce66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/835e48b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/28577ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Granville House Housatonic 10/10 Exceptional (86) "Beautiful rooms, wonderful hosts, been here several times and plan to come again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $314 CA $350 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Housatonic-Hotels-Granville-House.h50873824.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/bc78d43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/5fa6f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/3ff5efd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whistler's Inn Bed & Breakfast Lenox 7.8/10 Good (500) "Cozy spot with very friendly propeietor" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $318 CA $356 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/44792ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge Lee 9.8/10 Exceptional (98) "A first class little inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $451 CA $529 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn West Stockbridge 9.6/10 Exceptional (432) "Very casual and easy check in and out; lovely and substantial breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $149 CA $164 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (109) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $433 CA $524 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/ddc846d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Accessible (The Smithfield Room)](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/e3593a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/6cdeed48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 2 Bedrooms (The Dutchess Suite) | Private kitchen](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/bfcf4a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Pine Plains Pine Plains 9.8/10 Exceptional (297) "Very nice spacious room and a good value." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theodore CA $345 CA $390 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Pine-Plains-Hotels-Inn-At-Pine-Plains.h22227121.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/c93a1f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with digital channels, TV, DVD player](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/523420f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Ensuite (2nd Floor)](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/dc8b3c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/6f307fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Changing Times Boutique Country Lodging Craryville 10/10 Exceptional (108) "Great experience, looking forward to staying again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $244 CA $273 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Craryville-Hotels-Changing-Times-Boutique-Country-BB.h19185424.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn Lenox 9.4/10 Exceptional (162) "Inn was gorgeous and staff exceptional!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/2d151170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6cbad311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B Lee 10/10 Exceptional (133) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![3 bedrooms, bed sheets](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/84b174a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, bed sheets](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/2db66224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/9bacc168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/68cd085f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen Lenox CA $291 CA $427 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-Historic-Cornell-Inn-Cozy-Berkshires-Retreat-Lenox.h115169907.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/2028495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main Lenox 10/10 Exceptional (74) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $636 CA $711 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/1ca7ca84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Omega Special Sundays Thursdays 5 night's stay | Shared kitchen facilities](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/7e7882f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Twin Room | Living area](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/49be28f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/8f5460b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### it's a good thing Clinton Corners 8.0/10 Very good (24) "Wonderful stay and wonderful hosts! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniela-Cristina CA $188 CA $213 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Clinton-Corners-Hotels-Its-A-Good-Thing.h99919328.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/aeb97fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/a55bcd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/bd8601b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, Clinton Corners 8.2/10 Very good (11) "Beautiful, comfortable house on a lovely property. Hosts were very friendly and welcoming. Would definitely return and recommend to friends and family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $195 CA $271 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15®ionId=183683&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Bed-And-Breakfast.d183683-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Bed-And-Breakfast.d183683-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Hillsdale Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "This property was great for our weekend getaway. It is conveniently located " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent all the way around" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Excellent front desk staff. Ask for Steve. Very convenient to Monument Mountain and local ski resorts." [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Overlook Hotel](//images.trvl-media.com/lodging/119000000/118060000/118056600/118056521/88412f44_y.jpg) ### Overlook Hotel 10/10 Excellent "We were in town for a wedding and elected to stay at the family owned Overlook Hotel. This hotel is under renovation and coming along nicely. The rehabilitated buildings come with luxurious fixtures and relaxing decor. A perfect retreat! Being that it is just up and running, some ammentities will need to catch up. If your stay in the near future requires anything in particular, be sure to communicate with the owners- i am certain the be sure you have all you need!" [](https://expedia.ca/Saugerties-Hotels-Overlook-Hotel.h118056521.Hotel-Information) ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](//images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG 10/10 Excellent "Perfect spot for an overnight stay when coming to the area" [](https://expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-West-Coxsackie.h2591583.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Hillsdale ## Hillsdale B&B information | Number of reviews | 3,707 | | --- | --- | | Accommodation | 51 B&B | | Lowest Price | CA $164 | | Highest Price | CA $711 | ## 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](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information): 17.9 mi (28.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. [Lakehouse Inn](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information): 14 rooms. Situated 16.8 mi (27.1 km) from the heart of Hillsdale. Enjoy the free full breakfast and deli. [Shaker Mill Inn](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information): 9 rooms. 13.4 mi (21.6 km) from the heart of downtown.[Inn at Pine Plains](https://www.expedia.ca/Pine-Plains-Hotels-Inn-At-Pine-Plains.h22227121.Hotel-Information): 8 rooms. Located 15.3 mi (24.7 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. 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