Title: Chester B&B: Find the Best Bed and Breakfast from CA $298 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Black dirt region farm Chester New York](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/117bcdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/3cff05ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Primrose) | Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/0c3a1284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/f9a6b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast [](https://www.expedia.ca/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) Chester 9.2/10 Wonderful (233 reviews) "Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erek CA $298 CA $338 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/20894557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (146 reviews) "Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/30c7644a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/78872596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/9e133beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/cc3411cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Verde BB Greenwood Lake NY [](https://www.expedia.ca/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) Monroe 10/10 Exceptional (13 reviews) "Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $238 CA $298 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/0db4b471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/598f2dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/ecffd1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Quadruple Room, Ensuite (Violet Suite #10)](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/751f1365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alpine Haus Bed & Breakfast Inn [](https://www.expedia.ca/Vernon-Hotels-Alpine-Haus-Bed-Breakfast-Inn.h1587870.Hotel-Information) Vernon 9.2/10 Wonderful (327 reviews) "Excellent experience, all the way around. Quiet and quaint, all the modern amenities, excellent host and service, hot water in the shower, beautiful room, bountiful, delicious breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $278 CA $318 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Vernon-Hotels-Alpine-Haus-Bed-Breakfast-Inn.h1587870.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/952dd0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/c90ab9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/7aba0c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/1b99f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stagecoach Inn [](https://www.expedia.ca/Newburgh-Hotels-Stagecoach-Inn.h16065013.Hotel-Information) Goshen 9.6/10 Exceptional (79 reviews) "We only stayed one night, but it was very comfortable and the staff was friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $326 CA $402 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Newburgh-Hotels-Stagecoach-Inn.h16065013.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=2026-01-28&endDate=2026-01-29®ionId=6046665&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.d6046665-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.d6046665-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Cozy and quiet. Rooms need size. Surroundings idellic. Nature abounds." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Our stay was wonderful, and its always our go-to hotel when we are in the area and need a place to stay. The only comment was that the tub was super slippery without some type of bathmat in the bottom, as we almost had serious falls because of it. But that was the only thing, everything else was great. " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Great staffing, clean rooms!!!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Everything " [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Yanki was very helpful , attentive and friendly. The breakfast was lousy ! It was the same thing every day . They had coffee and tea available. Parking was easy . Clean room . " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "very nice room. Staff very responsive." [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Great" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg) ### Mountain Creek 10/10 Excellent "Cozy and comfortable bed!" [](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.Hotel-Information) ![Courtyard by Marriott Mahwah](https://images.trvl-media.com/lodging/1000000/20000/15300/15280/5299e3bb_y.jpg) ### Courtyard by Marriott Mahwah 10/10 Excellent "Great staff, clean spacious room, good fitness center" [](https://expedia.ca/Mahwah-Hotels-Courtyard-By-Marriott-Mahwah.h15280.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 563 | | ----------------- | ------- | | Accommodation | 12 B&B | | Lowest Price | CA $298 | | Highest Price | CA $402 | ## Frequently asked questions ### What are the most popular Chester B&Bs? ### What is the nightly rate for a B&B in Chester? ### What is the difference between a Chester B&B and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Harriman ](https://www.expedia.ca/2Star-Harriman-Hotels.s20-0-d183682.Travel-Guide-Filter-Hotels) - 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