Title: Chester B&B: Find the Best Bed and Breakfast from CA $179 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/5376b74ed08fb0cd0348035ae5ca74c9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Elizabeth Massa Peroulakis # Find a Bed and Breakfast in Chester from CA $179 - ![](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 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester B&B ![Room (Louis XIV)](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/9e954e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/babab812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8cf443f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Global Fusion)](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/0298eeb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Naomi's Inn Bed & Breakfast Liberty Heights 9.0/10 Wonderful (421) "Simple yet delicious and well executed breakfast. Perfectly cooked eggs. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $157 CA $179 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) ![Room, River View (The Williamsburg Suite) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/e7482ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/177e0ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/ff08161f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The River Walk Suite) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/c6249a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Mill Inn Hatfield 9.4/10 Exceptional (499) "Loved our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $551 CA $616 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Springfield-Hotels-Old-Mill-Inn.h1639314.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) ![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](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.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 (372) "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 $233 CA $260 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.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) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn Lee 9.6/10 Exceptional (289) "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 $241 CA $283 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.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/2000000/1200000/1197600/1197581/3ff5efd5.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) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/bc78d43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whistler's Inn Bed & Breakfast Lenox 7.8/10 Good (500) "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 $190 CA $212 total includes taxes & fees Nov 19 - Nov 20 [](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) ![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) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.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 $352 CA $413 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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) ![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 $592 CA $662 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.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) ![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) ### Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen Lenox CA $293 CA $428 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Historic-Cornell-Inn-Cozy-Berkshires-Retreat-Lenox.h115169907.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) ![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) ![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) ### 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) ![2 Bedrooms 1 Bath](https://images.trvl-media.com/lodging/39000000/38300000/38291200/38291154/9edc1253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38300000/38291200/38291154/c67dcf8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38300000/38291200/38291154/dfc4e525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Bedrooms 1 Bath | In-room dining](https://images.trvl-media.com/lodging/39000000/38300000/38291200/38291154/19a25a2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tanglewood Suites Stockbridge 6.4/10 (22) "NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $308 CA $308 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Stockbridge-Hotels-Tanglewood-Suites.h38291154.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) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.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 (110) "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 $537 CA $649 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.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) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.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 (53) "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 $332 CA $351 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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) ![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) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/0e806d18.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) ### Experience Timeless Elegance in The Edith Wharton Room! Lenox CA $294 CA $430 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Edith-Wharton-Room.h115241164.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/b0925eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/2f1ef067.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) ### Elegant Carriage House room with a queen bed and private patio. Lenox CA $316 CA $456 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Elegant-Carriage-House-Room-With-A-Queen-Bed-And-Private-Patio.h115241207.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) ![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) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/67e04fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/12a0d554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Carriage House room with a double bed and private balcony Lenox CA $338 CA $484 total includes taxes & fees Nov 20 - Nov 21 [](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) ![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) ![1 bedroom, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/e222ef75.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) ### Historic Susan B. Anthony Room - Cozy & Charming Stay Lenox CA $360 CA $514 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Historic-Susan-B-Anthony-Room-Cozy-Charming-Stay.h115241178.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/af794997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/31755c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/64c22087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/w1301h728x0y4-b0569205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn Lenox CA $462 CA $645 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Niles-Johnson-Room-At-The-Cornell-Inn.h115241126.Hotel-Information) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241192/a97b855e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241192/dbe22f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241192/8bc6f060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241192/ba1c0df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace Lenox CA $506 CA $697 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Elegant-Emily-Dickinson-Junior-Suite-With-King-Bed-Fireplace.h115241192.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241234/f2181b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241234/0e5c3882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241234/2dde0ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241234/b4757376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant suite with a king bed, fireplace, and kitchenette. Lenox CA $574 CA $783 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Elegant-Suite-With-A-King-Bed.h115241234.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241145/c9ca2020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241145/w446h732x0y0-22a9689e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241145/d7f33db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241145/05ab7e44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn Lenox CA $574 CA $783 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Experience-Luxury-In-The-Lady-Cicely-Grand-Suite-At-The-Cornell-Inn.h115241145.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=2025-12-02&endDate=2025-12-03®ionId=6005399&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%2FChester-Bed-And-Breakfast.d6005399-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Bed-And-Breakfast.d6005399-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ### Homewood Suites by Hilton Hadley Amherst 10/10 Excellent "Clean room, spacious room, nice staff, and good location for our trip. " [](https://expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information) ### Quality Inn West Springfield 10/10 Excellent "Very courteous staff. Comfortable, clean room. Always interesting people travelling through." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Berkshire Mountain Lodge 10/10 Excellent "The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ### Courtyard by Marriott West Springfield 10/10 Excellent "Work trip meet my needs" [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### The Ellery 10/10 Excellent "I stayed in a double queen room with my daughter on a visit to Smith. The room was very comfortable, the host was delightful l, and the breakfast was delicious! Will be back!" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ### Quality Inn Westfield - Springfield 10/10 Excellent "Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 2,318 | | --- | --- | | Accommodation | 32 B&B | | Lowest Price | CA $179 | | Highest Price | CA $783 | ## Frequently asked questions ### Searching for B&Bs in Chester? > If you're looking for something a little different than your standard hotel experience, a bed and breakfast could be the perfect alternative for your getaway. While you're enjoying your trip to Chester, you might want to explore the theater scene by catching a show at Chester Town Hall. ### Why would you choose B&Bs instead of traditional hotels? > Every B&B has its own unique feel. Whether it's a garden for guests to admire or a sunlit breakfast nook, the little details are what make bed and breakfasts the perfect escape. ### What are the best B&Bs in Chester? > Below are some well-liked B&Bs in the area: [The Cornell Inn, Lenox & The Berkshires](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information): 16.6 mi (26.7 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. [Chambery Inn](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information): 9 rooms. 14.1 mi (22.7 km) from the downtown core. Enjoy the private yard and deli. [Whistler's Inn Bed & Breakfast](https://www.expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information): 14 rooms. Situated 16.6 mi (26.7 km) from the heart of Chester. Enjoy the private yard and unique décor. [Lakehouse Inn](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information): 14 rooms. 14.8 mi (23.9 km) from the heart of downtown. Enjoy the free full breakfast and deli. ### When should I book my B&B in Chester? > When you're planning your escape to Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall. ### What is there to do in Chester? > If you want to check out some popular attractions in Chester, you might enjoy a visit to Chester Town Hall. Littleville Lake and Pyramid Lake are also some sites to visit if you want to see more of the area. ### How can I get to and around Chester? > You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. 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