Title: Cheshire B&B: Find the Best Bed and Breakfast from CA $169 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find a Bed and Breakfast in Cheshire from CA $169 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire B&B ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorie CA $352 CA $373 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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) ![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) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.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) ### Shaker Mill Inn West Stockbridge 9.6/10 Exceptional (430) "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 $154 CA $169 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/be3999ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/7a497aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trail in Adams - Berkshires’ Art Hotel Adams 8.8/10 Excellent (138) "We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $243 CA $271 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.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) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.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 (1000) "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 $179 CA $254 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/7b825179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/542dbb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Shared Dormitory](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/f69b88ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UU Rowe Camp and Conference Center Rowe CA $208 CA $220 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.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) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.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 (285) "Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $256 CA $300 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn Lee 9.6/10 Exceptional (370) "Amazing customer service! Location was very good to explore the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophia CA $239 CA $267 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/31000000/30320000/30314300/30314245/0504d1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/31000000/30320000/30314300/30314245/76eb8718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/31000000/30320000/30314300/30314245/77a5ec1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/31000000/30320000/30314300/30314245/86a0bf4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Door B&B Lee 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $245 CA $391 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Lee-Hotels-The-Red-Door-BB.h30314245.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/e961014f.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/5fa6f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whistler's Inn Bed & Breakfast Lenox 7.8/10 Good (499) "We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $187 CA $209 total includes taxes & fees Oct 30 - Oct 31 [](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) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $485 CA $569 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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) ![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) ![Room #10 Queen's Cottage | Private kitchen](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/bbf9b83e.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 (132) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $477 CA $533 total includes taxes & fees Nov 4 - Nov 5 [](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) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115170000/115170000/115169907/68cd085f.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/e10f13a2.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) ### Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen Lenox CA $290 CA $426 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Lenox-Hotels-Historic-Cornell-Inn-Cozy-Berkshires-Retreat-Lenox.h115169907.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) ![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) ![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) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $433 CA $524 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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) ![Suite, Private Bathroom (Tanglewood Suite)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.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 (161) "Inn was gorgeous and staff exceptional!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce CA $219 CA $245 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.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 $610 CA $682 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.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) ![Front of property](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/ca0080b3.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) ![Interior entrance](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/0fed38f6.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 $222 CA $249 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/4609a9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/1e673737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/9a87bae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/b0925eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant Carriage House room with a queen bed and private patio. Lenox CA $312 CA $454 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lenox-Hotels-Elegant-Carriage-House-Room-With-A-Queen-Bed-And-Private-Patio.h115241207.Hotel-Information) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/23b3990f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/976df379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/e8b9576b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/52586681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Timeless Elegance in The Edith Wharton Room! Lenox CA $290 CA $426 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Edith-Wharton-Room.h115241164.Hotel-Information) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/cab9849e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/66c88863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/67e04fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/0ab2702a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Carriage House room with a double bed and private balcony Lenox CA $335 CA $482 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Lenox-Hotels-Cozy-Carriage-House-Room-With-A-Double-Bed-And-Private-Balcony.h115241220.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/5094c384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/4d1c49db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/8e547a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/b9beadbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Susan B. Anthony Room - Cozy & Charming Stay Lenox CA $357 CA $512 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Lenox-Hotels-Historic-Susan-B-Anthony-Room-Cozy-Charming-Stay.h115241178.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=2025-11-07&endDate=2025-11-08®ionId=6005398&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%2FCheshire-Bed-And-Breakfast.d6005398-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Bed-And-Breakfast.d6005398-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean room " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Huttopia Berkshires ](//images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231_y.jpg) ### Huttopia Berkshires 10/10 Excellent "Healthy food too!" [](https://expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Nice clean and new. I had a nice stay, with restaurants across the street and a dunkin very close for the morning " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Parking was easy. Check in smooth, and the room was clean, attractive and comfortable," [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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 "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Yes" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ## Find out more about Cheshire ## Cheshire B&B information | Number of reviews | 2,740 | | --- | --- | | Accommodation | 35 B&B | | Lowest Price | CA $169 | | Highest Price | CA $682 | ## Frequently asked questions ### Searching for B&Bs in Cheshire? > If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit. ### Why would you choose a B&B versus a traditional hotel? > B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away. ### What are the best B&Bs in Cheshire? > Below are some well-liked B&Bs in the area: [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information): 6 rooms. 1.2 mi (2 km) from the heart of Cheshire. Enjoy the free full breakfast and unique décor. [The Cornell Inn, Lenox & The Berkshires](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information): 14.8 mi (23.9 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 17.1 mi (27.5 km) from the heart of Cheshire. Enjoy the free full breakfast and deli. [Chambery Inn](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information): 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. ### What's the best time of year to book my B&B in Cheshire? > When you're planning your stay in Cheshire, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Cheshire? > When you want to explore some things to do in Cheshire, consider a visit to Mount Greylock State Reservation. You might also consider a trip to sites like Mount Greylock State Reservation Visitor Center or Mount Greylock if you have time to see more of the area. ### How can I get to and around Cheshire? > Mapping out your trip in and around Cheshire is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. 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